Process and intermediates for preparing fungicidal imidazole diphenylaliphaticboranes and derivatives thereof

ABSTRACT

Organoborane imidazole compounds having the formula: ##STR1## wherein R, R 1 , R 2 , R 3 , R 4 , and X are defined in the description, and intermediates therefor are disclosed. 
     The compounds of formula I are especially useful as agricultural fungicides.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a division of copending application Ser. No. 450,872filed Dec. 14, 1989, now U.S. Pat. No. 4,983,589.

BACKGROUND OF THE INVENTION

This invention relates to certain diphenylaliphatic borane imidazolecomplexes and derivatives thereof. In a further aspect, the inventionrelates to the use of such complexes as agricultural fungicides.

A large amount of crop loss and plant damage is incurred each year dueto plant diseases caused by four classes of fungi: Ascomycetes, causinga large number of leaf spots, blights, soil-bourn and post-harvestdiseases; Deuteromycetes, also causing a large number of leaf spots,blights, soil-bourn and post-harvest diseases; Basidiomycetes, causingrust, smuts, bunts and soil borne-diseases; and Phycomycetes, causingdowny mildews, leaf blights and soil-bourn diseases.

Leaf spot and blight diseases, such as those induced by species ofLeptosphaeria, Mycosphaerella, Alternaria, and Helminthosporium causedamage to many crops such as maize, wheat, banana, and solanaceous cropsand are difficult to control.

Various species of the genus Botrytis are responsible for diseasescausing large losses in numerous vegetable, ornamental and vine crops.Present fungicides such as benzimidazoles and dicarboximides cannotadequately control these diseases due to the development of resistanceby the pathogen.

The late blights and downy mildew plant diseases produced, for example,by Phytophthora and Plasmopara are very destructive to grape andsolanaceous crops, e.g., potato, tomato. These diseases are alsodifficult to control due to the development of resistance to the leadingsystemic fungicides used to control these diseases.

Thus, it would be desirable to develop new fungicides which areeffective to control plant diseases and especially in the case of lateblights, mildew and Botrytis-produced diseases which are not subject tocross-resistance of the pathogen and which do not cause significantinjury to the plants (i.e., are relatively non-phytotoxic).

U.S. Pat. No. 3,062,708 generally teaches that amine complexes oftriphenylborane with certain Lewis bases have antifungal activity. Thepatent shows in vitro activity with respect to triphenylborane-imidazoleand illustrates in vivo activity against tomato early blight, bean rust,late blight and seed rot (Pythium ultimum) with respect to certaintriphenylborane amines including complexes with piperidine, pyridine and4-ethylpyridine.

U.S. Pat, No. 3,211,679 teaches that triarylborane amine complexes withpyridine or a variety of substituted pyridines are useful as toxicantsfor antifouling paint and that such paints import residual toxicity tomarine borers to wood structures.

U.S. Pat. No. 3,686,398 teaches that certain 10,9-boroxarophenanthrenesare useful to control fungi and exhibited preventative control of beanrust and celery late blight.

U.S. Pat. No. 3,696,103 teaches that certain di(substituted andunsubstituted phenyl)azaborolidines exhibit fungicidal, insecticidal,acaricidal and herbicidal activity The fungicidal activity is describedas polyvalent and is shown against bean anthracnose (Collectrotrichumlindemythianum), tomato mildew (late blight) (Phytophthora infestans),tobacco mildew (blue mold) (Peronospora tabaci), cucumber (powdery)mildew (Erysiphe cichoracearum) and wheat rust (Puccinia glumarum) atquantities of between 10 and 200 g of active substance per hectoliter ofliquid diluent such as water.

U.S. Pat. No. 4,613,373 teaches that certain tetra(substituted andunsubstituted phenyl) boranes complexed with a heterocyclic amine areuseful as antifouling, antiseptic, and antifungal agents in manyindustrial applications. In vitro inhibiting activity of certain ofpatentees compounds against certain fungi are shown in Table 4 of thepatent.

Based on the Derwent Abstract, Japanese Patent Application Publication62-277307 describes complexes of tri(substituted phenyl)borane withamines and nitrogen containing heterocycles as useful as insecticides,miticides and nematocides. Based on Derwent Abstract 5188957, JapanesePatent Application publication JP 1056684 published Mar. 3, 1989discloses certain tetraphenylboron-onium complexes useful asagricultural and industrial fungicides.

SUMMARY OF THE INVENTION

The present invention provides compounds having fungicidal activityagainst certain plant diseases and which exhibit no crop phytotoxicityor low levels of phytotoxicity which are within acceptable limits.Certain of the compounds exhibit protective or preventative activityagainst a broad spectrum of Botrytis diseases, mildews and blights andleafspot and leaf blights induced by Spetoria, and are not affected bycross-resistance of the pathogen to other fungicides. Certain of thecompounds further exhibit eradicant activity with respect to certainfungal diseases, for example, celery late blight.

The present invention provides organoborane imidazole complexes havingthe following formula (I) and intermediates of formula II hereinbelow:##STR2## wherein:

R is alkyl having 1 through 4 carbon atoms; cycloalkyl having 3 through6 carbon atoms; alkenyl having 2 through 6 carbon atoms; haloalkylhaving 1 through 4 carbon atoms and 1 through 4 halo substituentindependently selected from the group of fluoro, chloro, and bromo; orhaloalkenyl having 3 through 6 carbon atoms and 1 through 4 halo atomsindependently selected from the group of fluoro, chloro and bromo;

R¹ is hydrogen; alkyl having 1 through 12 carbon atoms; cycloalkylhaving 3 through 6 carbon atoms; lower alkenyl having 2 through 6 carbonatoms; haloalkyl having 1 through 4 carbon atoms and 1 through 3 haloatoms independently selected from the group of fluoro, chloro, bromo andiodo; haloalkenyl having 2 through 6 carbon atoms and 1 through 3 haloatoms independently selected from the group of fluoro, chloro, bromo andiodo; cyanoalkyl wherein the alkyl moiety has 1 through 4 carbon atoms,hydroxyalkyl having 1 through 6 carbon atoms and 1 hydroxy grouppreferably located at the terminal carbon atom of the alkyl group, loweralkoxyalkyl having 1 through 3 carbon atoms in the alkoxy moiety and 1through 3 carbon atoms in the alkyl moiety, lower alkoxycarbonylalkylhaving 1 through 3 carbon atoms in the alkoxy moiety and 1 through 3carbon atoms in the alkyl moiety; phenyl; substituted phenyl having 1through 4 substituents independently selected from the group of fluoro,chloro, bromo, iodo, lower alkyl having 1 through 6 carbon atoms andnitro with the proviso that said substituted phenyl has no more than twonitro substituents; aralkyl having 1 through 4 carbon atoms in the alkylmoiety and wherein the aryl moeity is phenyl; substituted benzyl having1 through 4 substituents on the phenyl moiety independently selectedfrom the group of fluoro, chloro, bromo, iodo, lower alkyl having 1through 6 carbon atoms and nitro with the proviso that said phenylmoiety has no more than two nitro substituents; and1,3-dioxolan-2-yl-alkyl in which the alkyl moiety has 1 through 4 carbonatoms;

R² is hydrogen; lower alkyl having 1 through 6 carbon atoms; phenyl,benzyl; or substituted benzyl having 1 through 4 substituents on thephenyl ring independently selected from the group of fluoro, chloro,bromo, iodo and alkyl having 1 through 6 carbon atoms;

R³ is hydrogen or alkyl having 1 through 6 carbon atoms with the provisothat when R⁴ is other than alkyl, then R³ is hydrogen;

R⁴ is hydrogen, alkyl having 1 through 6 carbon atoms, phenyl, orphenalkyl in which the alkyl moiety has 1 through 4 carbon atoms withthe proviso that at least two of R¹, R², R³ and R⁴ are hydrogen and thefurther proviso that when R³ is alkyl, then R⁴ is an alkyl groupidentical to the R³ alkyl group;

R⁵ and R⁶ are independently hydrogen or lower alkyl having 1 through 6carbon atoms; and

X and Y are independently selected from the group of hydrogen, alkylhaving 1 through 4 carbon atoms; fluoro; chloro; alkoxy having 1 through4 carbon atoms; alkylthio having 1 through 4 carbon atoms; or haloalkylhaving 1 through 4 carbon atoms and 1 through 3 halo substituentsindependently selected from the group of fluoro, chloro, and bromo andmay be at any available position on the respective phenyl rings.

In those cases where the complex of Formula I or the intermediates offormula II have an asymmetric carbon atom, the compounds can exist asoptical isomers. In some instances the compounds also exist as geometricisomers, for example, where R is an alkenyl group having a cis-transdouble bond. In some cases (e.g., where R¹ =H and R³ ≠R⁴), the compoundscan exist as coordination isomers wherein boron is coordinated to eitherthe N1 or N3 nitrogen.

The above formulas are intended to encompass the respective individualisomers as well as mixtures thereof and the respective isomers as wellas mixtures thereof are encompassed within the invention.

In a further aspect, the invention provides a fungicidal compositioncomprising a compatible carrier and a fungicidally effective amount ofthe compound(s) of the invention or mixtures thereof.

The invention also provides a method for preventing or controllingfungi, which comprises applying an amount of a compound of Formula I ormixtures thereof to such fungi or its habitat which is effective toprevent or inhibit or arrest the growth of the fungi.

In another aspect the invention provides a method for preventing orcontrolling fungal plant diseases which comprises applying to the plantan amount of the compound(s) of Formula I or mixtures thereof which iseffective to prevent or inhibit the growth of the fungal pathogenproducing the disease.

The present invention also provides chemical intermediates, e.g., thecompound of formula II, and processes for preparing the compounds ofFormula I.

The invention will be further described hereinbelow.

FURTHER DESCRIPTION OF THE INVENTION AND THE PREFERRED EMBODIMENTS

Illustrations of typical compounds of Formula I can be had by referenceto Examples 1-6 set forth hereinbelow on Pages 23-72.

In terms of fungicidal effectiveness and spectrum of activity, thepreferred compounds are those wherein R¹ is hydrogen, alkyl having 1through 6 carbon atoms, preferably 1 through 4 carbon atoms, alkenylhaving 2 through 6 carbon atoms, haloalkenyl having 2 through 6 carbonatoms and 1 through 3 halo atoms independently selected from the groupof fluoro, chloro, and bromo, lower hydroxyalkyl having 1 through 3carbon atoms and 1 hydroxy group, phenyl or aralkyl having 1 through 4carbon atoms in the alkyl moiety and the aryl moiety is phenyl; R², R³and R⁴ are independently hydrogen or alkyl having 1 through 6,preferably 1 through 3, carbon atoms; and X is hydrogen, alkyl having 1through 4 carbon atoms, with the proviso that at least two of R¹, R², R³or R⁴ are hydrogen.

Especially preferred in terms of the magnitude of antifungal activity orspectrum of antifungal activity, and/or crop safety are those compoundswherein R is alkyl or alkenyl, especially methyl and vinyl; R¹ ishydrogen or is an alkyl, cycloalkyl, alkenyl group having four or lesscarbon atoms, 2-hydroxyethyl or 2,2,2-trifluoroethyl and especiallyisopropyl, sec-butyl, t-butyl, cyclopropyl vinyl 2-hydroxyethyl and2,2,2-trifluoroethyl; R² is hydrogen. Also, in the case where R¹, R³,R⁴, X and Y are all hydrogen the compounds where R¹ is alkyl having 1through 4 carbon atoms generally exhibit good fungicidal activity.

The following compounds exhibit exceptionally excellent activity;(1-propylimidazole)-diphenylmethylborane;(1-isopropylimidazole)-diphenylmethylborane;(1-t-butylimidazole)-diphenylmethylborane;(1-cyclopropylimidazole)diphenylmethylborane;(1-2',2',2'-trifluoroethylimidazole)diphenylmethylborane;(1-t-butylimidazole)-diphenylvinylborane;(1-cyclopropylimidazole)-diphenylvinylborane; and(1-vinylimidazole)-diphenylvinylborane. These compounds exhibitexcellent preventative activity against a broad spectrum of fungaldiseases and especially so the first two compounds.

In terms of manufacturing ease, the compounds wherein X and Y are equaland are located at the same position of the respective phenyl arepreferred, i.e., (IA) ##STR3## wherein R, R¹, R², R³ and R⁴ are asdefined herein above with respect to formula I and Xl is hydrogen; alkylhaving 1 through 4 carbon atoms; fluoro; chloro; alkoxy having 1 through4 carbon atoms; alkylthio having 1 through 4 carbon atoms; or haloalkylhaving 1 through 4 carbon atoms and 1 through 3 halo substituentsindependently selected from the group of fluoro, chloro, and bromo; andwherein each of the X¹ groups is located at the same position of therespective phenyl rings to which they are attached.

Definitions

As used herein the following terms have the following meanings unlessexpressly stated to the contrary:

The term "alkyl" refers to both straight- and branched-chain alkylgroups. The term "lower alkyl" refers to alkyl groups having a total offrom 1 through 6 carbon atoms, preferably 1 through 4 carbon atoms andincludes primary, secondary and tertiary alkyl groups. Typical loweralkyls include, for example, methyl, ethyl, n-propyl, isopropyl,n-butyl, t-butyl, pentyl, hexyl and the like.

The term "lower alkylene" refers to both straight chained and branchedchained alkylene groups having 1 through 6 carbon atoms, preferably 1through 4 carbon atoms and includes, for example, ##STR4## The term"lower alkenyl" refers to alkenyl groups having 2 through 6, preferably2 through 4, carbon atoms and includes, for example, vinyl, 1-propenyl,2-propenyl, 1-methylvinyl, 1-butenyl, 2-methylprop-1-enyl and the like.

The term "lower alkoxy" refers to the group --OR' wherein R' is loweralkyl.

The term "lower alkoxyalkyl" refers to the group R'OR"- wherein R' andR" are independently straight chain or branched chain alkyl groupshaving 1 through 3 carbon atoms.

The term "lower alkylthio" refers to the group R'S- wherein R' is astraight chain or branched chain alkyl group having 1 through 3 carbonatoms.

The term "halo" refers to the group of fluoro, chloro, bromo and iodounless expressly defined as referring only to fluoro, chloro and bromo.

The term "aralkyl" refers to the group ##STR5## wherein R' is loweralkyl having 1 through 4 carbon atoms and preferably is methyl or ethyl.

The term "lower haloalkyl" refers to haloalkyl compounds having 1through 4 carbon atoms and 1 through 3 halo atoms independently selectedfrom the group of fluoro, chloro, bromo. Preferably the lower haloalkylgroup has 1 or 2 carbon atoms.

The term "3-substituted alkenyl" refers to the group --CH₂ CH═CHYwherein Y is the substituent.

In naming borane complexes the terms "diphenylalkylborane oralkyldiphenylborane" refer to the group ##STR6## wherein R is alkyl.

Similarly, the terms "diphenylalkenylborane, cycloalkyldiphenylborane,diphenylhaloalkyl, and diphenylhaloalkenyl" refer to the group ##STR7##wherein R is the named alkenyl, cycloalkyl, haloalkyl, or haloalkenylgroup.

The term "imidazole-diphenylmethylborane" refers to the compound##STR8## Since coordination at the N3 nitrogen is presumed in thisnomenclature.

The term "room temperature" or "ambient temperature" refers to about20°-25° C.

The term "compatible salts" refers to salts which do not significantlyadversely alter the fungicidal properties or plant safety of the parentcompound. Suitable salts include cation salts such as, for example, thecation salts of lithium, sodium, potassium, alkali earth metals,ammonia, quaternary ammonium salts, and the like.

Synthesis

The compounds of Formula I can be prepared by the followingschematically represented process: ##STR9## wherein R, R¹, R², R³, R⁴, Xand Y are as defined hereinabove, R⁵ and R⁶ are independently hydrogenor lower alkyl, preferably hydrogen or methyl, and Z is chloride,bromide or iodide.

Step 1 of this process is a Grignard reaction and typically is effectedby contacting Compound (A) with the Grignard Reagent (B) under reactiveconditions, preferably in an inert organic solvent under substantiallyanhydrous conditions. Typically, this step is conducted at temperaturesin the range of about from 15° C. to 80° C., preferably 20° C to 35° C.,for about from 2 to 24 hours, preferably about from 2 to 4 hours, usingabout from 1 to 3.5, preferably 1 to 3 moles of Grignard Reagent (B) permole of Compound (A).

Suitable organic solvents which can be used include, for example,tetrahydrofuran, alkyl ethers (e.g. ethyl ether), hexane, and the like,and compatible mixtures thereof. Best results are obtained usingtetrahydrofuran, ethyl ether or glyme as the solvent.

The second step can be effected by contacting intermediate II withimidazole (C), preferably in an inert organic solvent, under reactiveconditions. The second step can be conveniently conducted in situwithout separation of intermediate II.

Typically, this process is conducted at temperatures in the range ofabout from 20° C. to 35° C., preferably 20° C. to 25° C., for about from2 to 24 hours, preferably 10 to 24 hours, using about from 1 to 5,preferably 1 to 3 moles of Compound (C) per mole of Compound (B).Typically, about from 1 to 3 moles of base are used per mole of Compound(C).

Suitable inert organic solvents which can be used include, for example,the solvents listed above with respect to Step 1, and compatiblemixtures thereof. Since most conveniently, the second step is conductedin situ, the same solvent will generally be used in the second step asused in the first step.

The starting materials of Formulas (B) and (C) are generally knownmaterials and can be prepared by known procedures, or obviousmodifications thereof (i.e., substitution of appropriate startingmaterials). The preparation of starting materials (A) is, for example,described in Y. Rasiel and H. K. Zimmerman, Ann. 649,.111 (1961) or byR. L. Lestinger and I. Skoog, J. Am. Chem. Soc. 77, 2491 (1955), and inthe case where X, Y, R⁵ and R⁶ are hydrogen, is a commercially availablematerial. The starting materials of Formula B are Grignard Reagents andcan be prepared via standard procedures such as, for example, describedin P. E. Pearson, D. Cowan, J. D. Becker, J. Org. Chem. 24, 504 (1959).The starting materials of Formula C are substituted imidazoles can beprepared according to known procedures such as for example described inM. R. Grimmett, Advance in Heterocyclic Chem. 12, 103 (1970), Ibid. 27,241 (1980) and in many instances are commercially available. Forexample, the 1-substituted imidazoles are either commercially availableor can be prepared by alkylating the imidazole sodium salt with theappropriate alkyl halides in dimethylformamide. The 2-substitutedimidazoles are either commercially available or can be prepared by theclassical Radszizewski reaction with glyoxal, suitable aldehydes, andammonia in a single step. The 4-(5)-imidazoles are either commerciallyavailable or can be prepared by the Weidenhagen reaction of acetoxyketones with cupric acetate, formaldehyde, and ammonia. Di- ortri-substituted imidazoles can be prepared similarly. The di- ortri-substituted imidazole can be prepared by lithiating and alkylatingof mono-substituted imidazoles as described in B. H. Lipshutz, B. Huff,W. Hazen, Tetrahedron Letter 29, 3411 (1988).

The starting materials of Formula A can also be prepared by hydrolysisand oxidation of the corresponding optionally substitutedtriphenylborane alkali metal hydroxide adduct by procedure of P.Denisevich illustrated hereinbelow in Preparation A. In the case where Xand Y are different and/or are not located at the same position of therespective phenyl, the procedure described in D. Giraud et al, CompteRendus Hebdomadaires des Sceances de l'Academie des Sciences, p. 319 v.254 (1962) can be applied to prepare the compounds of formula I.

The compounds of Formula I also generally can be conveniently preparedvia the P. Kenny process using an exchange reaction of an imidazole witha diphenyl-alkylboron-ammonia complex: ##STR10## wherein R, R¹, R², R³,R⁴, X and Y are defined hereinabove.

In accordance with this process, Compound (D) is contacted with Compound(C) under reactive conditions, preferably in a inert organic solventunder substantially anhydrous conditions.

Preferably, this process is conducted at temperatures in the range ofabout from 0° C. to reflux, conveniently about 20° C. to 25° C. forabout 1 to 72 hours, using about from 0.1 to 1 moles of Compound (C) permole of Compound (D). Suitable inert organic solvents which can be usedinclude, for example, halogenated alkanes, for example, chloroform,methylene chloride; lower alkenols, for example, methanol, ethanol;acetone and the like and compatible mixtures thereof. The startingmaterial of Formula (D) can be prepared by known procedures such as, forexample, described by D. Giraud et al, Compte Rendus Hebdomadaires desSceances de l'Academie des Sciences, p. 319, v. 254 (1962), or byobvious modifications thereof (e.g., use of appropriately substitutedreactants and appropriate solvents).

Compound (D) can also be conveniently prepared via the reaction ofintermediate II with ammonia.

General Process Conditions

In the above-described processes, the products can be recovered from therespective reaction product mixtures by any suitable separation andpurification procedure, such as, for example, extraction, trituration,and recrystallization. Suitable separation and purification proceduresare, for example, illustrated in the Examples set forth hereinbelow.

Generally, the reactions described above are conducted as liquid phasereactions and hence pressure is generally not significant except as itaffects temperature (boiling point) where reactions are conducted atreflux. Therefore, these reactions are generally conducted at pressuresof about from 300 to 3,000 mm of mercury and conveniently are conductedat about atmospheric or ambient pressure.

It should also be appreciated that where typical or preferred processconditions (e.g., reaction temperatures, times, mole ratios ofreactants, solvents, pressures, etc.) have been given, that otherprocess conditions could also be used unless otherwise stated. Optimumreaction conditions (e.g., temperature, reaction time, mole ratios,solvents, etc.) may vary with the particular reagents or organicsolvents, used but can be determined by routine optimization procedures.

Where optical isomer mixtures are obtained, the respective opticalisomers can be obtained by conventional resolution procedures. Geometricisomers and coordination isomers can be separated by conventionalseparation procedures which depend upon differences in physicalproperties between the isomers.

Utility

The compounds of the present invention are effective in controllingfungal plant diseases, including downy mildew, leaf blights, leaf spots,damping-off diseases, Botrytis diseases, and post-harvest diseases.Certain of the compounds further exhibit a broad spectrum of activity.The compounds are generally more effective as preventative fungicidesand a number of which are especially effective in preventing grey mold(Botrytis), grape downy mildew, late blights in solanaceous crops, andSeptoria leaf spot diseases.

The compounds are applied to the subject plants in fungicidallyeffective amounts. When applied as preventative fungicides, thecompounds are preferably applied at prescheduled times prior to thedetection of plant infection or immediately upon the detection ofinfection. The optimum fungicidally effective amount will, of course,depend on several factors such as the host, the type of fungus, weatherconditions, and the particular compound of the invention. Generally,however, the compounds are preferably applied at a rate of about from0.2 to 2.5 kg per hectare for preventative application, and 1 to 3 kgper hectare for eradicant application. The compounds may also be appliedfor seed treatments. Generally, the compounds are applied as seedtreatments at a rate of about 0.5 to 32 g per 100 kg of seeds. As withmost pesticidal compounds, the fungicides of the invention are notusually applied full strength, but are generally incorporated withconventional, biologically inert extenders or carriers normally employedfor facilitating dispersion of active fungicidal compounds, recognizingthat the formulation and mode of application may affect the activity ofthe fungicide. Thus, the fungicides of the invention may be formulatedand applied as granules, as powdery dusts, as wettable solutions, asemulsifiable concentrates, as solutions, or as any of several otherknown types of formulations, depending on the desired mode ofapplication.

Wettable powders are in the form of finely divided particles whichdisperse readily in water or other dispersant. These compositionsnormally contain from about 5% to 80% fungicide, and the rest inertmaterial, which includes dispersing agents, emulsifying agents andwetting agents. The powder may be applied to the soil as a dry dust, orpreferably as a suspension in water. Typical carriers include fuller'searth, kaolin clays, silicas, and other highly absorbent, readilywettable, inorganic diluents. Typical wetting, dispersing or emulsifyingagents include, for example: the aryl and alkylaryl sulfonates and theirsodium salts; alkylamide sulfonates, including fatty methyl taurides;alkylaryl polyether alcohols, sulfated higher alcohols, and polyvinylalcohols; polyethylene oxides, sulfonated animal and vegetable oils;sulfonated petroleum oils, fatty acid esters of polyhydric alcohols andthe ethylene oxide addition products of long-chain mercaptans andethylene oxide. Many other types of useful surface-active agents areavailable in commerce. The surface-active agent, when used, normallycomprises from 1% to 15% by weight of the fungicidal composition.

Dusts are freely flowing admixtures of the active fungicide with finelydivided solids such as talc, natural clays, kieselguhr, pyrophyllite,chalk, diatomaceous earths, calcium phosphates, calcium and magnesiumcarbonates, sulfur, lime, flours, and other organic and inorganic solidswhich act as dispersants and carriers for the toxicant. These finelydivided solids have an average particle size of less than about 50microns. A typical dust formulation useful herein contains 75% silicaand 25% of the toxicant.

Useful liquid concentrates include the emulsifiable concentrates, whichare homogeneous liquid or paste compositions which are readily dispersedin water or other dispersant, and may consist entirely of the fungicidewith a liquid or solid emulsifying agent, or may also contain a liquidcarrier such as xylene, heavy aromatic naphthas, isophorone, and othernonvolatile organic solvents. For application, these concentrates aredispersed in water or other liquid carrier, and are normally applied asa spray to the area to be treated.

Other useful formulations for fungicidal applications include simplesolutions of the active fungicide in a dispersant in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene, or other organic solvents. Granularformulations, wherein the fungicide is carried on relatively courseparticles, are of particular utility for aerial distribution or forpenetration of cover-crop canopy. Pressurized sprays, typically aerosolswherein the active ingredient is dispersed in finely divided form as aresult of vaporization of a low-boiling dispersant solvent carrier, suchas the Freons, may also be used. All of those techniques for formulatingand applying fungicides are well known in the art. The percentages byweight of the fungicide may vary according to the manner in which thecomposition is to be applied and the particular type of formulation, butin general comprise 0.05% to 95% of the toxicant by weight of thefungicidal composition, and depending on whether the composition isintended for direct application or dilution prior to application. Thecompounds are typically applied at rates in the range of about from 0.1to 5 kg/hectare, preferably 0.2 to 3 kg/hectare, and typically areapplied as foliage sprays.

The fungicidal compositions may be formulated and/or applied with otheringredients, including wetting agents, emulsifiers, adjuvants,stabilizers, etc., as well as other compatible active ingredients suchas other fungicides, insecticides, nematocides, bactericides, plantgrowth regulators, fertilizers, etc.

A further understanding of the invention can be had in the followingnon-limiting Preparation(s) and Example(s). Wherein, unless expresslystated to the contrary, all temperatures and temperature ranges refer tothe Centigrade system and the term "ambient" or "room temperature"refers to about 20°-25° C. The term "percent" or "%" refers to weightpercent and the term "mole" or "moles" refers to gram moles. The term"equivalent" refers to a quantity of reagent equal in mole equivalentsto the mole equivalent of the preceding or succeeding reactant recitedin that example or preparation in terms of finite moles or finite weightor volume. Where given, proton-magnetic resonance spectrum (p.m.r. orn.m.r.) were determined at 90 and 360 mHz, signals are assigned assinglets (s), broad singlets (bs), doublets (d), double doublets (dd),triplets (t), double triplets (dt), quartets (q), and multiplets (m);and cps refers to cycles per second.

PREPARATIONS AND EXAMPLES PREPARATION A 2-Aminoethyl Diphenyborinate##STR11## This preparation illustrates the preparation of the titlecompound via the method of P. Denisevich, Jr.

Aqueous 10 wt% hydrochloric acid is slowly added to 250 g of a solutioncontaining 22.5 g of triphenylborane.sodium hydroxide. The addition ofhydrochloric acid is continued until a pH of 1.2. During the addition,cooling is provided to maintain the temperature of the reaction mixturebelow 30° C. Eighty (80) ml of ethyl ether is added and the mixturestirred overnight (about 10-12 hours) at room temperature during whichtime a slow steady stream of air is passed through the mixture. Fifty(50) ml of ethyl ether is added to compensate for evaporation losses Thereaction mixture forms a two-phase system. The ethyl ether phase isseparated, washed with water and then added to 4.9 g of 2-aminoethanol.The mixture is stirred for one hour at room temperature and thenfiltered. The recovered solids are washed with water, affording 14.4 gof the title compound m.p. 186°-188° C.

EXAMPLE 1 (1-Isopropylimidazole)-Diphenylmethylborane ##STR12## In thisexample, 2.25 g (0.01 mol) of 2-aminoethyl diphenylborinate is added to35 mL of ethyl ether at room temperature followed by the dropwiseaddition of 0.03 mol of methylmagnesium chloride. The mixture is stirredfor three hours at room temperature and then 3.3 g (0.03 mol) ofisopropylimidazole is added and stirred overnight (12-14 hours) at roomtemperature. The reaction product mixture is mixed with 100 mL ofsaturated aqueous ammonium chloride solution and 200 mL of ethyl etheraffording a two-phase mixture. The layers are separated and the aqueouslayer is combined with the separated ether layer, washed with water,extracted with 100 ml of ethyl ether. The extract is dried overmagnesium sulfate, and filtered. The filtrate is evaporated to give asolid which is recrystalized from cold dichloromethane and dried invacuo to give 2.20 g (76.2% yield) of a white solid, m.p. 180°-182° C.

Similarly, by following the same general procedure using the appropriatestarting materials, the following compounds can be prepared:

imidazole-diphenylethylborane;

imidazole-diphenylbutylborane;

imidazole-diphenylisopropylborane;

imidazole-diphenylcyclohexylborane;

(1-methylimidazole)-diphenylmethylborane;

(1-t-butylimidazole)-diphenylethylborane;

(1-octylimidazole)-diphenyl(trifluoromethyl)borane;

(1-decylimidazole)-diphenylethylborane;

(1-dodecylimidazole)-diphenyl(4-chlorobutyl)borane;

[1-(2-ethyl-4,6-dimethyl)heptylimidazole]-diphenylisopropylborane;

(1-cyclopropylimidazole)-diphenylcyclohexylborane;

(1-cyanomethylimidazole)-diphenylmethylborane;

[1-(2-cyanopropyl)imidazole]-diphenylethylborane;

[1-(4-cyanobutyl)imidazole]-diphenylbutylborane;

(1-methoxymethylimidazole-diphenylisopropylborane;

(1-phenylimidazole)-diphenylcyclohexylborane;

[1-(2-phenylethyl)imidazole]-diphenylmethylborane;

[1-(4-bromophenyl)imidazole]-diphenylethylborane;

[1-(2-chlorophenyl)imidazole]-diphenylisopropylborane;

1-(β-hydroxyethylimidazole)-diphenylpropylborane;

[1-(4-cyclohexylphenyl)imidazole-diphenylcyclohexylborane;

[1-(2,6-dimethylphenyl)imidazole-diphenylmethylborane;

[1-(3-propoxycarbonylpropyl)imidazole]-diphenyl(1-chloro-2-fluoroethyl)borane;

[1-(2-chloro-4-fluorophenyl)imidazole]-diphenylethylborane;

[1-(4-fluoro-2-methylphenyl)imidazole-diphenyl(4-bromobutyl)borane;

[1-(3-chloroallyl)imidazole-diphenylisopropylborane;

[1-(2-fluoropent-2-enyl)imidazole]-diphenylcyclohexylborane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]imidazole)-diphenylmethylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazolediphenyl(1-bromo-2-chloroethyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylbutylborane;

[1-(2-ethoxypropyl)imidazole]-diphenylisopropylborane;

[1-(2-ethylcarbonylpropyl)imidazole]-diphenylisopropylborane;

[1-(2-chloro-4-nitrobenzyl)imidazole]-diphenylcyclopropylborane;

[1-(4-fluoro-3-methyl-2-nitrobenzyl)imidazole]-diphenyl-t-butylborane;

[1-(3-isopropylpropoxy)imidazole]-diphenylcyclohexylborane;

(2-ethylimidazole)-diphenylmethylborane;

(2-pentylimidazole)-diphenylisopropylborane;

(2-phenylimidazole)-diphenylmethylborane;

(2-benzylimidazole)-diphenylethylborane;

[2-(4-bromobenzyl)imidazole]-diphenylbutylborane;

[2-(3-ethylbenzyl)imidazole]-diphenylisopropylborane;

[2-(2-bromobenzyl)imidazole]-diphenylcyclohexylborane;

[2-(2,6-dimethylbenzyl)imidazole]-diphenylmethylborane;

[2-(2,4-dichlorobenzyl)imidazole]-diphenylethylborane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-diphenylbutylborane;

[2-(2-chloro-3-iodobenzyl)imidazole]-diphenylcyclohexylborane;

[5-(4-methylpentyl)imidazole]-diphenylmethylborane;

(5-isopropylimidazole)-diphenylethylborane;

(5-t-butylimidazole)-diphenylbutylborane;

(5-ethylimidazole)-diphenylisopropylborane;

(5-methylimidazole)-diphenylcyclohexylborane;

(5-isopropylimidazole)-diphenylmethylborane;

(5-cyclohexylimidazole)-diphenylethylborane;

(5-ethylimidazole)-diphenylbutylborane;

(5-isopropylimidazole)-diphenylisopropylborane;

(5-t-butylimidazole)-diphenylcyclohexylborane;

(5-phenylimidazole)-diphenylmethylborane;

(5-benzylimidazole)-diphenylethylborane;

(5-β-phenethyl)-diphenylbutylborane;

(5-α-phenylpropyl)-diphenylisopropylborane;

imidazole-di(2-methylphenyl)ethylborane;

imidazole-di(3-isopropylphenyl)butylborane;

imidazole-di(4-fluorophenyl)isopropylborane;

(1-methylimidazole)-di(3-ethylphenyl)t-butylborane;

(1-octylimidazole)di(2-chlorophenyl)methylborane;

(1-dodecylimidazole)di(2-methoxyphenyl)butylborane;

[1-(2-ethyl-4,6-dimethylheptyl)imidazole]-di(4-t-butylthiophenyl)isopropylborane;

(1-cyclopropylimidazole)di(4-1',1',2'-trichloroethylphenyl)cyclohexylborane;

(1-cyanomethylimidazole-di(3-trifluoromethylphenyl)methylborane;

[1-(2-cyanopropyl)imidazole]-di(2-methylphenyl)ethylborane;

[1-(4-cyanobutyl)imidazole]-di(3-isopropylphenyl)butylborane;

(1-methoxymethylimidazole)-di(4-fluorophenyl)isopropylborane;

[1-(2-phenylethyl)imidazole]-di(2-chlorophenyl)methylborane;

[1-(4-bromophenyl)imidazole]-di(3-fluorophenyl)ethylborane;

[1-(2-chlorophenyl)imidazole]-di(2-methoxyphenyl)isopropylborane;

[1-(4-cyclohexylphenyl)imidazole]-di(4-t-butylthiophenyl)cyclohexylborane;

[1-[4-chloro-4-fluorophenyl)imidazole]-di(3-trifluoromethylphenyl)ethylborane;

[1-4fluoro-2-methylphenyl)imidazole]-di(2-methylphenyl)butylborane;

[1-(3-chloroallyl)imidazole]-di(isopropylphenyl)isopropylborane;

[1-(2-fluoropent-2-enyl)imidazole]-di(4-fluorophenyl)cyclohexylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-di(2-chlorophenyl)ethylborane;

[1-(2-ethoxypropyl)imidazole]-di(2-methoxyphenyl)isopropylborane;

[1-(3-isopropoxypropyl)imidazole]-di(4-butylthiophenyl)cyclohexylborane;

(2-methylimidazole)-di(2-ethoxyphenyl)methylborane;

(2-benzylimidazole)-di(3-trifluoromethylphenyl)ethylborane;

[2-(4-bromobenzyl)imidazole]-di(2-methylphenyl)butylborane;

[2-(3-ethylbenzyl)imidazole]-di(3-isopropylphenyl)isopropylborane;

[2-(2-bromobenzyl)imidazole]-di(4-fluorophenyl)cyclohexylborane;

[2-(2,6-dimethylbenzyl)imidazole]-di(3-chlorophenyl)methylborane;

[2-(2,4-dichlorobenzyl)imidazole]-di(2-chlorophenyl)ethylborane;

[2-(2-chloro-3-iodobenzyl)imidazole]-di(2-methoxyphenyl)cyclohexylborane;

[5-(4-methylpentyl)imidazole]-di(4-t-butylthiophenyl)methylborane;

(5-t-butylimidazole)-di(2-methylphenyl)butylborane;

(5-ethylimidazole)-di(3-trifluoromethylphenyl)ethylborane;

(5-methylimidazole)-di(3-isopropylphenyl)cyclohexylborane;

(5-isopropylimidazole-di(4-fluorophenyl)methylborane;

(5-isopropylimidazole)-di(3-chlorophenyl)isopropylborane;

(5-t-butylimidazole)-di(2-methoxyphenyl)cyclohexylborane;

(5-phenylimidazole)-di(3-fluorophenyl)ethylborane;

(5-2'-phenylpropylimidazole)-di(3-ethoxyphenyl)borane;

(1-methyl-2-phenylimidazole)-diphenylmethylborane;

(2-ethyl-1-t-butylimidazole)-diphenylethylborane;

(2-benzyl-1-octylimidazole)-diphenylmethylborane;

(2-4'-chlorobenzyl-1-decylimidazole)-diphenylethylborane;

(1-dodecyl-2-p-fluorobenzylimidazole)-diphenylbutylborane;

[1-(2-ethyl-4,6-dimethyl)-2-(2-chloro-4-fluorobenzyl)heptylimidazole]-diphenylisopropylborane;

(1-cyclopropyl-2-2'-methylbenzylimidazole)-diphenylcyclohexylborane;

(1-cyanomethyl-2-3'-hexylbenzylimidazole)-diphenylmethylborane;

[1-(2-cyanopropyl)-2-(2,6-dimethylbenzyl)imidazole]diphenylethylborane;

[1-(4-cyanobutyl)imidazole-2-(2-chloro-4-fluorobenzyl)]diphenylbutylborane;

(1-methoxymethylimidazole)-diphenylisopropylborane;

1-phenyl-2-p-bromobenzylimidazole)-diphenylcyclohexylborane;

[2-(2-iodobenzyl)-1-(2-phenylethyl)imidazole]-diphenylmethylborane;

[1-(4-bromophenyl)imidazole]-diphenylethylborane;

[1-(2-chlorophenyl)imidazole]-diphenylisopropylborane;

(1-β-hydroxyethyl-5-methylimidazole)-diphenylpropylborane;

[1-(4-cyclohexylphenyl)-5-butylimidazole]-diphenylcyclohexylborane;

[5-benzyl-1-(2,6-dimethylphenyl)imidazole]-diphenylmethylborane;

[1-(2-chloro-4-fluorophenyl)-5-isopropylimidazole]-diphenylethylborane;

[1-(4-fluoro-2-methylphenyl)-5-phenylimidazole]-diphenylbutylborane;

[1-(3-chloroallyl)-5-β-phenylethylimidazole]-diphenylisopropylborane;

[1-(2-fluoropent-2-enyl)-5-(2-phenylpentyl)imidazole]diphenylcyclohexylborane;

(5-butyl-1-[2-(1,3-dioxolan-2-yl)ethyl]imidazole)-diphenylmethylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-5-methylimidazole)-diphenylethylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-5-phenylimidazole)-diphenylbutylborane;

[1-(2-ethoxypropyl)-5-isopropylimidazole]-diphenylisopropylborane;

[1-(3-isopropoxypropyl)-5-phenylimidazole]-diphenylcyclohexylborane;

(5-butyl-2-ethylimidazole)-diphenylmethylborane;

(5-methyl-2-pentylimidazole)-diphenylisopropylborane;

(2-phenyl-5-phenylimidazole)-diphenylmethylborane;

(2-benzylimidazole)-diphenylethylborane;

[2-(4-bromobenzyl)-5-(2-phenylbutyl)imidazole]-diphenylbutylborane;

[2-(3-ethylbenzyl)-5-isopropylimidazole]-diphenylisopropylborane;

[2-(2-bromobenzyl)-5-hexylimidazole]-diphenylcyclohexylborane;

[2-(2,6-dimethylbenzyl)-5-methylimidazole]-diphenylmethylborane;

[2-(2,4-dichlorobenzyl)-5-t-butylimidazole]-diphenylethylborane;

[5-benzyl-2-(3-fluoro-5-ethylbenzyl)imidazole]-diphenylbutylborane;

[2-(2-chloro-3-iodobenzyl)imidazole]-diphenylcyclohexylborane;

[4,5-dimethylimidazole]-diphenylmethylborane;

[4,5-di-(t-butyl)imidazole]-diphenylethylborane;

(4,5-diethylimidazole)-diphenylbutylborane;

(4,5-dipentylimidazole)-diphenylisopropylborane;

(5-methylimidazole)-diphenylcyclohexylborane;

[4,5-di(isopropyl)imidazole]-diphenylmethylborane;

(4,5-diethylimidazole)-diphenylbutylborane;

(4,5-dipentylimidazole)-diphenylisopropylborane;

(4,5-dipentylimidazole)-diphenylcyclohexylborane;

(4-methyl-4,5-dihexylimidazole)-diphenylmethylborane;

[4,5-di(sec-butyl)-pentylimidazole]-diphenylethylborane;

[4,5-(isopropyl)-imidazole]-diphenylbutylborane;

(4,5-diethylimidazole)-diphenylisopropylborane;

(1,2-methylimidazole)-di(3-ethylphenyl)t-butylborane;

(5-methyl-1-octylimidazole)-di(2-chlorophenyl)methylborane;

(1-dodecyl-5-phenylimidazole)-di(2-methoxyphenyl)butylborane;

[1-(2-ethyl-4,6-dimethylheptyl)-5-propylimidazole]di(4-t-butylthiophenyl)isopropylborane;

(1-cyclopropyl-5-3,hexylimidazole)-di(4-1,,1,,2,-trichloroethylphenyl)cyclohexylborane;

(1-cyanomethyl-2-phenylimidazole)-di(3-trifluoromethylphenyl)methylborane;

[1-(2-cyanopropyl)-5-phenylimidazole)-di(2-methylphenyl)ethylborane;

[1-(4-cyanobutyl)-2-p-fluorophenylimidazole)-di(3-isopropylphenyl)butylborane;

(1-methoxymethyl-2-σ-methylimidazole)-di(4-fluorophenyl)isopropylborane;

[1-(2-phenylethyl)-5-(3-phenylpentyl)imidazole]-di(2-chlorophenyl)methylborane;

[1-(4-bromophenyl)-5-methylimidazole]di(2-fluorophenyl)ethylborane;

[1-(2-chlorophenyl)-5-isopropylimidazole]-di(2-methoxyphenyl)isopropylborane;

[1-(4-cyclohexylphenyl)-5-benzylimidazole]-di(4-t-butylthiophenyl)cyclohexylborane;

[1-(2-chloro-4-fluorophenyl)-5-methylimidazole]-di(3-trifluoromethylphenyl)ethylborane;

[1-(4-fluoro-2-methylphenyl)-5-isopropylimidazole]di(2-methylphenyl)butylborane;

[1-(3-chloroallyl)-5-ethylimidazole]-di(isopropylphenyl)isopropylborane;

[1-(2-fluoropent-2-enyl)-5-phenylimidazole]-di(4-fluorophenyl)cyclohexylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-5-phenylimidazole)-di(2-chlorophenyl)ethylborane;

[1-(2-ethoxypropyl)-5-β-phenylethylimidazole]-di(2-methoxyphenyl)isopropylborane;

[1-(3-isopropoxypropyl)-5-methylimidazole]-di(4-butylthiophenyl)cyclohexylborane;

(1,2-dimethylimidazole)-di(2-ethoxyphenyl)methylborane;

(2-benzyl-1-methylimidazole)-di(3-trifluoromethylphenyl)ethylborane;

[2-(4-bromobenzyl)-5-phenylimidazole]-di(2-methylphenyl)butylborane;

[2-(3-ethylbenzyl)-5-methylimidazole]-di(3-isopropylphenyl)isopropylborane;

[2-(2-bromobenzyl)-5-isopropylimidazole]-di(4-fluorophenyl)cyclohexylborane;

[5-benzyl-2-(2,6-dimethylbenzyl)imidazole]-di(3-chlorophenyl)methylborane;

[1-methyl-2-(2,4-dichlorobenzyl)imidazole]-di(2-chlorophenyl)ethylborane;

[4,5-di(t-butyl)imidazole]-di(2-methylphenyl)butylborane;

(4,5-diethylimidazole)-di(3-trifluoromethylphenyl)ethylborane;

(4,5-dimethylimidazole)-di(3-isopropylphenyl)cyclohexylborane;

(4,5-dipentylimidazole)-di(4-fluorophenyl)methylborane;

[4,5-di(isopropyl)imidazole]-di(2-chlorophenyl)isopropylborane;

[4,5-di(t-butyl)imidazole)-di(2-methoxyphenyl)cyclohexylborane;

(4,5-dihexylimidazole)-di(3-fluorophenyl)ethylborane;

(4-butyl-5-2'-phenylpropylimidazole)-di(3-ethoxyphenyl)borane;

imidazole-phenyl(σ-tolyl)methylborane;

imidazole-(4-fluorophenyl)phenylethylborane;

imidazole-diphenylbutylborane;

imidazole-(2-chlorophenyl)phenylisopropylborane;

imidazole-(3-methoxyphenyl)phenylcyclohexylborane;

(1-methylimidazole)-(2-ethylthiophenyl)phenylmethylborane;

(1-t-butylimidazole)-(4-trifluoromethylphenyl)phenylethylborane;

(1-octylimidazole)-(3-isopropylphenyl)phenylmethylborane;

(1-decylimidazole)-(3-fluorophenyl)phenylethylborane;

(1-dodecylimidazole)-(phenyl)(2-propoxyphenyl)butylborane;

[1-(2-ethyl-4,6-dimethyl)heptylimidazole]-(4-butylphenyl)phenylisopropylborane;

(1-cyclopropylimidazole)-(4-1',2',2'-trichlorophenyl)phenylcyclohexylborane;

(1-methoxymethylimidazole-phenyl-(2-isopropoxyphenyl)isopropylborane;

(1-phenylimidazole)-phenyl(3-methylthiophenyl)cyclohexylborane;

[1-(2-phenylethyl)imidazole]-(3-4'-bromobutylphenyl)phenylmethylborane;

[1-(4-bromophenyl)imidazole]-phenyl(4-propylphenyl)ethylborane;

1-(β-hydroxyethylimidazole)-phenyl(2-methoxyphenyl)propylborane;

[1-(4-cyclohexylphenyl)imidazole-(2-t-butylthiophenyl)phenylcyclohexylborane;

[1-(2,6-dimethylphenyl)imidazole-(3-chloromethylphenyl)phenylmethylborane;

[1-(3-propoxycarbonylpropyl)imidazole]-phenyl(p-tolyl)ethylborane;

[1-(4-fluoro-2-methylphenyl)imidazole-(2-ethoxyphenyl)phenylbutylborane;

[1-(3-chloroallyl)imidazole-phenyl(2-propylthiophenyl)isopropylborane;

[1-(2-fluoropent-2-enyl)imidazole]-phenyl(2-trifluoromethylphenyl)cyclohexylborane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]imidazole)-(2-fluorophenyl)phenylmethylborane;

[1-(2-ethoxypropyl)imidazole]-(2-bromomethylphenyl)phenylisopropylborane;

[1-(2-ethylcarbonylpropyl)imidazole]-(3-isopropylphenyl)phenylisopropylborane;

[1-(2-chloro-4-nitrobenzyl)imidazole]-(4-methoxyphenyl)phenylcyclopropylborane;

[1-(4-fluoro-3-methyl-2-nitrobenzyl)imidazole]-(2-isopropylthiophenyl)phenyl-t-butylborane;

[1-(3-isopropoxypropyl)imidazole]-phenyl(σ-tolyl)cyclohexylborane;

(2-ethylimidazole)-(2-methoxyphenyl)phenylmethylborane;

(2-phenylimidazole)-(3-ethylthiophenyl)phenylmethylborane;

(2-benzylimidazole)-diphenylethylborane;

[2-(4-bromobenzyl)imidazole]-phenyl(2-trifluoromethylphenyl)butylborane;

[2-(3-ethylbenzyl)imidazole]-(3-ethylphenyl)phenylisopropylborane;

[2-(2,6-dimethylbenzyl)imidazole]-phenyl(tolyl)methylborane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-(3-ethoxylphenyl)phenylbutylborane;

[5-(4-methylpentyl)imidazole]-phenyl(p-tolyl)methylborane;

(5-isopropylimidazole)-(3-chlorophenyl)phenylethylborane;

(5-t-butylimidazole)-(2-isopropoxyphenyl)phenylbutylborane;

(5-cyclohexylimidazole)-(4-isopropylthiophenyl)phenylethylborane;

(5-phenylimidazole)-(3-2'-bromo-3'-chloropropylphenyl)phenylmethylborane;

(5-benzylimidazole)-phenyl(m-tolyl)ethylborane;

(5-β-phenethyl)-(3-butoxyphenyl)phenylbutylborane;

imidazole-(2-methylphenyl)(p-tolyl)ethylborane;

imidazole-(4-fluorophenyl)(2-methoxylphenyl)isopropylborane;

(1-methylimidazole)-(3-ethylphenyl)(2-fluorophenyl)t-butylborane;

(1-octylimidazole)(2-chlorophenyl)(4-ethylthiophenyl)methylborane;

(1-dodecylimidazole)(2-methoxyphenyl)(3-t-butylphenyl)butylborane;

[1-(2-ethyl-4,6-dimethylheptyl)imidazole]-(3-t-butylphenyl)-(4-t-butylthiophenyl)isopropylborane;

(1-cyclopropylimidazole)(p-tolyl)(4-1',1',2'-trichloroethylphenyl)cyclohexylborane;

(1-cyanomethylimidazole-(3-trifluoromethylphenyl)(4-trifluoromethylphenyl)methylborane;

(1-methoxymethylimidazole)-(4-fluorophenyl)(2-chlorophenyl)isopropylborane;

[1-(2-phenylethyl)imidazole]-(2-chlorophenyl)methylborane;

[1-(4-bromophenyl)imidazole]-(2-bromomethylphenyl)(3-methoxyphenyl)ethylborane;

[1-(2-chlorophenyl)imidazole]-di(2-methoxyphenyl)isopropylborane;

[1-(4-cyclohexylphenyl)imidazole]-(4-t-butylthiophenyl)-(4-methoxyphenylcyclohexylborane;

(5-t-butylimidazole)-(2-methylphenyl)(3-fluorophenyl)butylborane;

(5-ethylimidazole)-(2-methylthiophenyl)(3-trifluoromethylphenyl)ethylborane;

(5-phenylimidazole)-(3-fluorophenyl)(3-ethylphenyl)ethylborane;

(5-2'-phenylpropylimidazole)-di(3-ethoxyphenyl)trifluoromethylborane;

(1-methyl-2-phenylimidazole)-diphenyl(2,2-dichloroethyl)borane;

[1-(2-ethyl-4,6-dimethyl)-2-(2-chloro-4-fluorobenzyl)heptylimidazole]-phenyl(σ-tolyl)isopropylborane;

(1-cyclopropyl-2-2,-methylbenzylimidazole)-(4-fluorophenyl)phenylcyclohexylborane;

[1-(2-cyanopropyl)-2-(2,6-dimethylbenzyl)imidazole]-(3-methoxyphenyl)phenylethylborane;

(5-butyl-2-ethylimidazole)-phenyl(p-tolyl)methylborane;

[4-methyl-5-(4-methylpentyl)imidazole]-(2-ethoxyphenyl)phenylmethylborane;

(5-cyclohexyl-4-methylimidazole)-(3-chlorophenyl)phenylethylborane;

(1,2-methylimidazole)-(3-ethylphenyl)(4-propoxyphenyl)-t-butylborane;

(5-methyl-1-octylimidazole)-(2-chlorophenyl)(3-trifluoromethylphenyl)methylborane;

(1-dodecyl-5-phenylimidazole)-(2-methoxyphenyl)(2-ethylthiophenyl)butylborane;

[1-(2-ethyl-4,6-dimethylheptyl)-5-propylimidazole]-(4-t-butylthiophenyl)(2-ethylphenyl)isopropylborane;

[4,5-di(isopropyl)imidazole]-(2-chlorophenyl)(4-propylthiophenyl)isopropylborane;and

(5-t-butyl-4-isopropylimidazole)-(2-methoxyphenyl)-(2-chlorophenyl)cyclohexylborane.

EXAMPLE 2 (1-Vinylimidazole) Diphenylvinylboron ##STR13##

In this example, 2.25 g (0.01 mol) of 2-aminoethyl diphenylborinate isdissolved in 30 ml of tetrahydrofuran at room temperature followed bythe dropwise addition of 0.03 mol of vinylmagnesium bromine over afifteen-minute period. The mixture is stirred for two hours at roomtemperature and then 0.01 mol of 1-vinylimidazole is added. The mixtureis stirred for about 18 hours at room temperature and then quenched bythe addition of 40 ml of aqueous 5% hydrochloric acid. The mixture isextracted twice with 40 ml of ethyl ether. The extracts are combined,washed with water and saturated aqueous sodium chloride solution, thendried over magnesium sulfate, filtered, and evaporated to dryness,affording a tan solid. The solid is washed with 60 ml of cold ethylether and 60 ml of hexane, and dried in vacuo affording 2.25 g of thetitle compound as a white powdery solid, m.p. 160°-161° C.

Similarly, by following the same general procedure using the appropriatestarting materials, the following compounds can be prepared:

imidazole-diphenylallylborane;

imidazole-diphenyl(2-methylbut-4-enyl)borane;

imidazole-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

imidazole-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

(1-octylimidazole)-diphenylvinylborane;

(1-decylimidazole)-diphenylallylborane;

(1-dodecylimidazole)-diphenyl(2-methylbut-4-enyl)borane;

(1-hydroxymethylimidazole)-diphenylvinylborane;

[1-(2-ethyl-4,6-dimethylheptyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

(1-cyclopropylimidazole)-diphenyl(4-chloro-5-fluorohex-2enyl)borane;

(1-cyanomethylimidazole)-diphenylvinylborane;

[1-(2-cyanopropyl)imidazole]-diphenylallylborane;

[1-(4-cyanobutyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

(1-methoxymethylimidazole)-diphenyl(5,5,5-trifluoropent-3enyl)borane;

(1-phenylimidazole)-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

[1-(2-phenylethyl)imidazole]-diphenylvinylborane;

[1-(4-bromophenyl)imidazole]-diphenylallylborane;

[1-(2-chlorophenyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[1-(4-hexylphenyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[1-(2,6-dimethylphenyl)imidazole]-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

[1-(2-chloro-4-fluorophenyl)imidazole]-diphenylvinylborane;

[1-(4-fluoro-2-methylphenyl)imidazole]-diphenylallylborane;

[1-(3-chloroallyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[1-(2-fluoropent-2-enyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]imidazole)-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylvinylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylallylborane;

[1-(2-ethoxypropyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[1-(3-isopropoxypropyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[1-(2-phenylethyl)imidazole]-diphenylvinylborane;

(2-benzylimidazole)-diphenylvinylborane;

[2-(4-bromobenzyl)imidazole]-diphenylallylborane;

[2-(4-ethylbenzyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[2-(2-bromobenzyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[2-(2,6-dimethylbenzyl)imidazole]-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

[2-(2,4-dichlorobenzyl)imidazole]-diphenylvinylborane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-diphenylallylborane;

[2-(2-chloro-3-iodobenzyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[5-(4-methylpentyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

(5-isopropylimidazole)-diphenyl(4-chloro-5-fluorohex-2-enylborane;

(5-t-butylimidazole)-diphenylvinylborane;

(5-ethylimidazole)-diphenylallylborane;

(5-methylimidazole)-diphenyl(2-methylbut-4-enyl)borane;

(5-isopropylimidazole)-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

(5-hexylimidazole)-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

(5-ethylimidazole)-diphenylvinylborane;

(5-isopropylimidazole)-diphenylallylborane;

(5-t-butylimidazole)-diphenyl(2-methylbut-4-enyl)borane;

imidazole-di(2-methylphenyl)allylborane;

imidazole-di(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

imidazole-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

imidazole-di(3-chlorophenyl)(4-chloro-5-fluorohex-2-enyl)borane;

(1-octylimidazole)-di(2-chlorophenyl)vinylborane;

(1-decylimidazole)-di(2-fluorophenyl)allylborane;

(1-dodecylimidazole)-di(2-methoxyphenyl)(2-methylbut-4-enyl)borane;

(1-ethyl-4,6-dimethylheptylimidazole)-di(2-t-butylthiophenyl)(5,5,5-trifluoropent-3-enyl)borane;

(1-cyclopropylimidazole)-di(4-1',1',2',2'-tetrachloroethylphenyl)(4-chloro-5-fluorohex-2-enyl)borane;

(1-cyanomethylimidazole)-di(3-trifluoromethylphenyl)vinylborane;

[1-(2-cyanopropyl)imidazole]-di(2-methylphenyl)allylborane;

[1-(4-cyanobutyl)imidazole]-di(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

(1-methoxymethylimidazole)-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

(1-phenylimidazole)-di(3-chlorophenyl)(4-chloro-5-fluorohex-2-enyl)borane;

[1-(2-phenylethyl)imidazole]-di(2-chlorophenyl)vinylborane;

[1-(2-chlorophenyl)imidazole]-di(2-methoxyphenyl)(2-methylbut-4-enyl)borane;

[1-(4-hexylphenyl)imidazole]-di(4-t-butylthiophenyl)(5,5,5-trifluoropent-3-enyl)borane;

[1-(2-chloro-4-fluorophenyl)imidazole]-di(3-trifluoromethylphenyl)vinylborane;

[1-(1-fluoro-2-methylphenyl)imidazole]-di(2-methylphenyl)allylborane;

[1-(3-chloroallyl)imidazole]-di(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

1-(2-fluoropent-2-enyl)imidazole]-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-di(2-chlorophenyl)vinylborane;

[1-(2-ethoxypropyl)imidazole]-di(2-methoxyphenyl)(2-methylbut-4-enyl)borane;

[1-(3-isopropylpropoxy)imidazole]-di(4-t-butylthiophenyl)-(5,5,5-trifluoropent-3-enyl)borane;

(2-benzylimidazole)-di(3-trifluoromethylphenyl)vinylborane;

[2-(4-bromobenzyl)imidazole]-di(2-methylphenyl)allylborane;

[2-(3-ethylbenzyl)imidazole]-di(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

[2-(2-bromobenzyl)imidazole]-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

[2-(2,4-dichlorobenzyl)imidazole]-di(2-chlorophenyl)ethylborane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-di(2-fluorophenyl)butylborane;

[2-(2-chloro-3-iodobenzyl)imidazole]-di(2-methoxyphenyl)(2-methylbut-4-enyl)borane;

[5-(4-methylpentyl)imidazole]-di(4-t-butylthiophenyl)5,5,5-trifluoropent-3-enyl)borane;

(5-t-butylimidazole)-di(3-trifluoromethylphenyl)vinylborane;

(5-ethylimidazole)-di(2-methylphenyl)allylborane;

(5-methylimidazole)-di(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

(5-isopropylimidazole)-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

(5-hexylimidazole)-di(3-iodophenyl)(4-chloro-5-fluorohex-2enyl)borane;

(5-ethylimidazole)-di(2-chlorophenyl)vinylborane;

(5-t-butylimidazole)-di(2-methoxyphenyl)(2-methylbut-4enyl)borane;

(1,2-dimethylimidazole)-diphenylvinylborane;

(1-isopropyl-2-methylimidazole)-diphenylvinylborane;

(2-butyl-1-octylimidazole)-diphenylvinylborane;

(1-decyl-2-phenylimidazole)-diphenylallylborane;

(2-benzyl-1-dodecylimidazole)-diphenyl(2-methylbut-4-enyl)borane;

(1-hydroxymethyl-p-fluorobenzylimidazole)-diphenylvinylborane;

[1-(2-chloro-4-fluorobenzyl)-1-(2-ethyl-4,6-dimethylheptyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[1-cyclopropyl(2,6-dimethylbenzyl)imidazole]-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

(1-cyanomethyl-5-methylimidazole)-diphenylvinylborane;

[1-(2-cyanopropyl)-5-propylimidazole]-diphenylallylborane;

[1-(4-cyanobutyl)-5-isopropylimidazole]-diphenyl(2-methylbut-4-enyl)borane;

(5-butyl-1-methoxymethylimidazole)-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

(1,5-diphenylimidazole)-diphenyl(4-chloro-5-fluorohex-2enyl)borane;

[5-ethyl-1-(2-phenylethyl)imidazole]-diphenylvinylborane;

[1-(4-bromophenyl)-5-isopropylimidazole]-diphenylallylborane;

[1-(2-chlorophenyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[1-(4-hexylphenyl)-5-β-phenylethylimidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[1-(2,6-dimethylphenyl)-5-methylimidazole]-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

[1-(2-chloro-4-fluorophenyl)-5-phenylimidazole]-diphenylvinylborane;

[1-(4-fluoro-2-methylphenyl)imidazole]-diphenylallylborane;

[1-(3-chloroallyl)-5-isopropylimidazole]-diphenyl(2-methylbut-4-enyl)borane;

[1-(2-fluoropent-2-enyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]-5-methylimidazole)-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-2-methylimidazole)-diphenylvinylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-5-phenylimidazole)-diphenylallylborane;

[1-(2-ethoxypropyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[5-ethyl-1-(3-isopropoxypropyl)imidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[5-benzyl-1-(2-phenylethyl)imidazole]-diphenylvinylborane;

(2-benzyl-5-methylimidazole)-diphenylvinylborane;

[2-(4-bromobenzyl)-5-propylimidazole]-diphenylallylborane;

[2-ethylbenzyl-5-(3-pentyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[2-(2-bromobenzyl)-5-phenylimidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[2-(2,6-dimethylbenzyl)-5-isopropylimidazole]-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

[2-(2,4-dichlorobenzyl)-5-(2,2-dimethylbutyl)imidazole]diphenylvinylborane;

[2-(3-fluoro-5-ethylbenzyl)-5-phenylimidazole]-diphenylallylborane;

[5-benzyl-2-(2-chloro-3-iodobenzyl)imidazole]-diphenyl(2-methylbut-4-enyl)borane;

[4,5-diethylimidazole]-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

(4,5-dimethylimidazole)-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

(4,5-diisopropylimidazole)-diphenylvinylborane;

(4,5-dipentylimidazole)-diphenylallylborane;

(4,5-dibutylimidazole)-diphenyl(2-methylbut-4-enyl)borane;

(4,5-dimethylimidazole)-diphenyl(5,5,5-trifluoropent-3-enyl)borane;

[4,5-di(3,3-dimethylbutyl)imidazole]-diphenyl(4-chloro-5-fluorohex-2-enyl)borane;

(4,5-diethylimidazole)-diphenylvinylborane;

(5-isopropylimidazole)-diphenylallylborane;

(4,5-dihexylimidazole)-diphenyl(2-methylbut-4-enyl)borane;

(4,5-dimethylimidazole)-diphenylvinylborane;

(4,5-diisopropylimidazole)-diphenylallylborane;

(1-octyl-5-methylimidazole)-di(2-chlorophenyl)vinylborane;

(1-decyl-5-methylimidazole)-di(2-fluorophenyl)allylborane;

(1-dodecyl-5-methylimidazole)-di(2-methoxyphenyl)(2-methylbut-4-enyl)borane;

(1-ethyl-4,6-dimethylheptyl-5-methylimidazole)-di(2-t-butylthiophenyl)-5,5,5-trifluoropent-3-enyl)borane;

(1-cyclopropyl-5-methylimidazole)-di(4-1',1',2',2'-tetrachloroethylphenyl)(4-chloro-5-fluorohex-2-enyl)borane;

(1-cyanomethyl-5-methylimidazole)-di(3-trifluoromethylphenyl)vinylborane;

[1-(2-cyanopropyl)-5-methylimidazole]-di(2-methylphenyl)allylborane;

[1-(4-cyanobutyl)-5-phenylimidazole]-di(3-isopropylphenyl)-(2-methylbut-4-enyl)borane;

(1-methoxymethyl-5-phenylimidazole)-di(4-fluorophenyl)-(5,5,5-trifluoropent-3-enyl)borane;

(1-phenyl-5-phenylimidazole)-di(3-chlorophenyl)(4-chloro-5-fluorohex-2-enyl)borane;

[1-(2-phenylethyl-5-phenylimidazole)-di(2-chlorophenyl)vinylborane;

[1-(2-chlorophenyl)-2-methylimidazole]-di(2-methoxyphenyl)-(2-methylbut-4-enyl)borane;

[1-(4-hexylphenyl)-2-methylimidazole]-di(4-t-butylthiophenyl)(5,5,5-trifluoropent-3-enyl)borane;

[1-(2-chloro-4-fluorophenyl)-2-phenylimidazole]-di(3-trifluoromethylphenyl)vinylborane;

[1-(1-fluoro-2-methylphenyl)-2-phenylimidazole]-di(2-methylphenyl)allylborane;

[1-(3-chloroallyl)-2-phenylimidazole]-di(3-isopropylphenyl)-(2-methylbut-4-enyl)borane;

[1-(2-fluoropent-2-enyl)-2-phenylimidazole]-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-2-phenylimidazole)-di(2-chlorophenyl)vinylborane;

[5-benzyl-1-(2-ethoxypropyl)imidazole]-di(2-methoxyphenyl)-(2-methylbut-4-enyl(borane;

[2-(2-bromo-3-chlorobenzyl)-1-(3-isopropylpropoxy)imidazole]di(4-t-butylthiophenyl)(5,5,5-trifluoro-3-enyl)borane;

(2-benzyl-5-methylimidazole)-di(3-trifluoromethylphenyl)vinylborane;

[2-(4-bromobenzyl)-5-phenylimidazole]-di(2-methylphenyl)allylborane;

2-(3-ethylbenzyl)-5-α-phenylpropylimidazole]-di(3isopropylphenyl)(2-methylbut-4-enyl)borane;

[2-(2-bromobenzyl)-5-isopropylimidazole]-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

[2-(2,4-dichlorobenzyl)-5-ethylimidazole]-di(2-chlorophenyl)ethylborane;

[2-(3-fluoro-5-ethylbenzyl)-5-isopropylimidazole]-di(2fluorophenyl)butylborane;

[2-(2-chloro-3-iodobenzyl)-5-phenylimidazole]-di(2-methoxyphenyl)(2-methylbut-4-enyl)borane;

[4-ethyl-5-[4-methylpentyl)imidazole]-di(4-t-butylthiophenyl)(5,5,5-trifluoropent-3-enyl)borane;

[(4,5-di(t-butyl)imidazole)-di(3-trifluoromethylphenyl)vinylborane;

(4,5-dihexylimidazole)-di(2-methylphenyl)allylborane;

(4,5-dimethylimidazole)-di(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

(4,5-dimethylimidazole)-di(4-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

(4,5-diethylimidazole)-di(3-chlorophenyl)(4-chloro-5-fluorohex-2-enyl)borane;

(4,5-dihexylimidazole)-di(2-chlorophenyl)vinylborane;

(4,5-dipropylimidazole)-di(2-methoxyphenyl)(2-methylbut-4-enyl)borane;

imidazole-phenyl(m-tolyl)allylborane;

imidazole-(3-methoxyphenyl)phenyl(2-methylbut 4-enyl)borane;

imidazole-(4-chlorophenyl)phenyl(5,5,5-trifluoropent-3-enyl) borane;

imidazole-(2-t-butylphenyl)phenyl(4-chloro-5-fluorohex-2-enyl)borane;

(1-ethylimidazole)-phenyl(2-trifluoromethylphenyl)vinylborane;

(1-decylimidazole)-(2-ethylphenyl)phenylallylborane;

(1-hydroxymethylimidazole)-(2-ethoxylphenyl)phenylvinylborane;

[1-(2-ethyl-4,6-dimethylheptyl)imidazole]-(4-ethylthiophenyl)phenyl(5,5,5-trifluoropent-3-enyl)borane;

(1-cyclopropylimidazole)-[4-(2-bromo-3-fluoropropyl)phenyl]phenyl(4-chloro-5-fluorohex-2-enyl)borane;

(1-cyanomethylimidazole)-(4-isopropylphenyl)phenylvinylborane;

(1-methoxymethylimidazole)-(3-isopropylthiophenyl)phenyl(5,5,5-trifluoropent-3-enyl)borane;

(1-phenylimidazole)-(2-propylphenyl)phenyl(4-chloro-5-fluorohex-2-enyl)borane;

[1-(2-phenylethyl)imidazole]-(3-fluorophenyl)phenylvinylborane;

[1-(4-bromophenyl)imidazole]-(4-methoxylphenyl)phenylallylborane;

[1-(2,6-dimethylphenyl)imidazole]-(3-isopropylthiophenyl)phenyl(4-chloro-5-fluorohex-2-enyl)borane;

[1-(2-chloro-4-fluorophenyl)imidazole]-(2-ethylphenyl)phenylvinylborane;

[1-(4-fluoro-2-methylphenyl)imidazole]-(3-2,-chloro,3'-bromobutylphenyl)phenylallylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylallylborane;

[1-(2-ethoxypropyl)imidazole]-(4-ethoxyphenyl)phenyl(2-methylbut-4-enyl)borane;

[1-(3-isopropoxypropyl)imidazole]-(3-methylthiophenyl)phenyl(5,5,5-trifluoropent-3-enyl)borane;

[1-(2-phenylethyl)imidazole]-(4-trifluoromethylphenyl)phenylvinylborane;

[5-(4-methylpentyl)imidazole]-phenyl(p-tolyl)(5,5,5-trifluoropent-3-enyl)borane;

(5-t-butylimidazole)-(4-t-butoxyphenyl)phenylvinylborane;

(5-ethylimidazole)-(3-chlorophenyl)phenylallylborane;

(5-methylimidazole)-(2-methoxylphenyl)phenyl(2-methylbut-4-enyl)borane;

imidazole-(2-ethylphenyl)(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

imidazole-(4-fluorophenyl)(3-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

imidazole-(3-chlorophenyl)(3-fluorophenyl)(4-chloro-5-fluorohex-2-enyl)borane;

(1-octylimidazole)-(2-chlorophenyl)(2-methylthiophenyl)vinylborane;

(1-dodecylimidazole)-(2-methoxyphenyl)(2-2',2'-dichloroethylphenyl)(2-methylbut-4-enyl)borane;

(1-ethyl-4,6-methylheptylimidazole)-(2-t-butylthiophenyl)(3-ethylphenyl)(5,5,5-trifluoropent-3-enyl)borane;

(1-cyclopropylimidazole)-(2-methoxyphenyl)(4-1',1',2',2'-tetrachloroethylphenyl)(4-chloro-5-fluorohex-2-enyl)borane;

(1-cyanomethylimidazole)-(3-trifluoromethylphenyl)(4-trifluoromethylphenyl)vinylborane;

[1-(2-cyanopropyl)imidazole]-(2-methylphenyl)(4-methylphenyl)allylborane;

[1-(4-cyanobutyl)imidazole]-di(3-isopropylphenyl)(2-methylbut-4-enyl)borane;

(2-benzylimidazole)-(2-ethylphenyl)(3-trifluoromethylphenyl)vinylborane;

[2-(4-bromobenzyl)imidazole]-(2-methylphenyl)(4-proxyphenyl)allylborane;

[2-(2,4-dichlorobenzyl)imidazole]-(2-chlorophenyl)(2-fluorophenyl)ethylborane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-(2-methoxyphenyl)(2-methylthiophenyl)butylborane;

[5-(4-methylpentyl)imidazole]-(4-t-butylthiophenyl)(3chlorophenyl)5,5,5-trifluoropent-3-enyl)borane;

(1,2-dimethylimidazole)-phenyl(3-propylphenyl)vinylborane;

[1-(4-hexylphenyl)-5-β-phenylethylimidazole]-phenyl(2-fluorophenyl)(5,5,5-trifluoropent-3-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]-5-methylimidazole)-(4-isopropylthiophenyl)phenyl(4-chloro-5-fluorohex-2-enyl)borane;

[2-(3-fluoro-5-ethylbenzyl)-5-phenylimidazole]-phenyl(3-trifluoromethylphenyl)allylborane;

(1-cyanomethyl-5-methylimidazole)-(2-chlorophenyl)(3-trifluoromethylphenyl)vinylborane;

[1-(2-cyanopropyl)-5-methylimidazole]-(2-methylphenyl)(2-methoxyphenyl)allylborane;

(1-phenyl-5-phenylimidazole)-(3-methylphenyl)(4-trifluoromethylphenyl)(4-chloro-5-fluorohex-2-enyl)borane;

(2-benzyl-5-methylimidazole)-(2-methoxyphenyl)(3-trifluoromethylphenyl)vinylborane;

(4,5-dihexylimidazole)-(3-chlorophenyl)(4-isopropylphenyl)(4-chloro-5-fluorohex-2-enyl)borane;and

(4,5-dipropylimidazole)-(2-methoxyphenyl)(2-1',2'2'-trichloroethylphenyl)(2-methylbut-4-enyl)borane.

Examples 3-5 illustrate the preparation of the present compounds via theP. Kenny exchange procedure.

EXAMPLE 3 (1-Isopropenylimidazole)-Diphenylvinylborane ##STR14##

a. 150 mL's of a 1.0 M vinylmagnesium bromide solution in THF is addedover 30 minutes to a solution of 11.25 g (50 mmol) diphenylboronic acidethanolamine complex in 100 mL's of THF. The addition is conducted sothat the reaction mixture became warm to the touch but did not reflux.After stirring for two hours and cooling to room temperature 8.0 mL, 57mmol of triethylamine is added and the reaction stirred overnight atroom temperature. 125 mL of a saturated aqueous solution of ammoniumchloride is carefully added dropwise to quench the reaction. 10 to 20 mLof water is added after the addition to solubilize the solids that hadformed. The quenched reaction is stirred vigorously for two hours atroom temperature whereupon the resulting liquid-liquid layers areseparated and the aqueous layer extracted with 100 mL of ether.. Thecombined organic layers are washed with 100 mL of saturated aqueoussodium chloride solution, dried over magnesium sulfate, filtered, andconcentrated to give a yellow paste. The paste is triturated overnightwith 60 mL of chloroform, and the resulting crystals are isolated bysuction filtration to give one crop of diphenylmethylboron-ammoniacomplex as 13 a white solid, 5.65 g, 27 mmol, 54%, m.p. 169°-172° C.

b. 1.51 g (7.22 mmol) of diphenylvinylboron-ammonia complex and 780milligrams (7.22 mmol) of 1-isopropenylimidazole in 50 mL of chloroformis stirred at room temperature for one hour. The chloroform is removedby evaporation under reduced pressure and the resultant white solidtriturated with 25 mL of methanol overnight. The resulting crystals arecollected via suction filtration and dried in vacuo to afford 1.9 g ofthe title compound, m.p. 149°-150° C.

Similarly, by following the same general procedure using the appropriatestarting materials, the following compounds can be prepared:

imidazole-diphenylhex-3-enylborane;

imidazole-diphenyl(3-chloroallyl)borane;

imidazole-diphenyl(3-bromobut-2-enyl)borane;

imidazole-diphenyl(3-methylbut-4-enyl)borane;

(1-octylimidazole)-diphenyl(1-isopropenyl)borane;

(1-decylimidazole)-diphenylhex-3-enylborane;

(1-dodecylimidazole)-diphenyl(3-chloroallyl)borane;

[1-(2-ethyl-4,6-dimethylheptyl)imidazole]-diphenyl(3-bromobutenyl)borane;

(1-cyclopropylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

(1-cyanomethylimidazole)-diphenylisopropenylborane;

[1-(2-cyanopropyl)imidazole]-diphenylhex-3-enylborane;

[1-(4-cyanobutyl)imidazole]-diphenyl(3-chloroallyl)borane;

(1-methoxymethylimidazole)-diphenyl(3-bromobut-2-enyl)borane;

(1-phenylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

[1-(2-phenylethyl)imidazole]-diphenyl(1-isopropenyl)borane;

[1-(4-bromophenyl)imidazole]-diphenylhex-3-enylborane;

[1-(2-chlorophenyl)imidazole]-diphenyl(3-chloroallyl)borane;

[1-(4-hexylphenyl)imidazole-diphenyl(3-bromo-2-enyl)borane;

[1-(2,6-dimethylphenyl)imidazole]-diphenyl(3-methylbut-1-enyl)borane;

[1-(2-chloro-4-fluorophenyl)imidazole]-diphenyl(1-isopropenyl)borane;

[1-(4-fluoro-2-methylphenyl)imidazole]-diphenylhex-3-enylborane;

[1-(3-chloroallyl)imidazole]-diphenyl(chloroallyl)borane;

[1-(2-fluoropent-2-enyl)imidazole]-diphenyl(3-bromobut-2-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]imidazole)-diphenyl(3-methylbut-1-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylisopropenylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylhex-3-enylborane;

[1-(2-ethoxypropyl)imidazole]-diphenyl(3-chloroallyl)borane;

[1-(3-isopropoxypropyl)imidazole]-diphenyl(3-bromobut-2-enyl)borane;

[1-(2-phenylethyl)imidazole]-(3-methylbut-1-enyl)borane;

(2-benzylimidazole)-diphenylisopropenylborane;

[2-(4-bromobenzyl)imidazole]-diphenyl(hex-3-enyl)borane;

(2-ethylbenzyl)imidazole-diphenyl(3-chloroallyl)borane;

[2-(2-bromobenzyl)imidazole]-diphenyl(3-bromobut-2-enyl)borane;

[2-(2,6-dimethylbenzyl)imidazole]-diphenyl(3-methylbut-1-enyl)borane;

[2-(2,4-dichlorobenzyl)imidazole]-diphenylisopropenylborane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-diphenylhex-3-enylborane;

[2-(2-chloro-3-iodobenzyl)imidazole]-diphenyl(3-chloroallyl)borane;

[5-(4-methylpentyl)imidazole]-diphenyl(3-bromobut-2-enyl)borane;

(5-isopropylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

(5-t-butylimidazole)-diphenylisopropenylborane;

(5-ethylimidazole)-diphenylhex-3-enylborane;

(5-methylimidazole)-diphenyl(3-chloroallyl)borane;

(5-isopropylimidazole)-diphenyl(3-bromobut-2-enyl)borane;

(5-hexylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

(5-ethylimidazole)-diphenylisopropenylborane;

(5-isopropylimidazole)-diphenylhex-3-enylborane;

(5-t-butylimidazole)-diphenyl(3-chloroallyl)borane;

imidazole-di(2-methylphenyl)hex-3-enylborane;

imidazole-di(3-isopropylphenyl)(3-chloroallyl)borane;

imidazole-di(4-fluorophenyl)3-bromobut-2-enyl)borane;

(1-octylimidazole)-di(2-chlorophenyl)isopropenylborane;

(1-dodecylimidazole)-di(Z-methoxyphenyl)(3-chloroallyl)borane:

(1-2'-ethyl-4',6'-dimethylheptylimidazole)-di(2-t-butylthiophenyl)(3-bromobut-2-enyl)borane

(1-cyanomethylimidazole)-di(3-trifluoromethylphenyl)(1-isopropenyl)borane:

1-(2-cyanopropyl)imidazole-di(2-methylphenyl)hex-3-enylborane:

[1-(4-cyanobutyl)imidazole]-di(3-isopropylphenyl)(3-chloroallyl)borane;

(1-methoxymethylimidazole)-di(4-fluorophenyl)(3-bromobut-2-enyl)borane;

[1-(2-phenylethylimidazole)-di(2-chlorophenyl)isopropenylborane;

[1-(2-chlorophenyl)imidazole]-di(2-methoxyphenyl)(3-chloroallyl)borane;

[1-(4-hexylphenyl)imidazole]-di(4-t-butylthiophenyl)(3-bromobut-2-enyl)borane;

[1-(2-chloro-4-fluorophenyl)imidazole]-di(3-trifluoromethylphenyl)isopropenylborane;

[1-(1-fluoro-2-methylphenyl)imidazole]-di(2-methylphenyl)hex-3-enylborane;

[1-(3-chloroallyl)imidazole]-di(3-isopropylphenyl)(3-chloroallyl)borane;p0[1-(2-fluoropent-2-enyl)imidazole]-di(4-fluorophenyl)(3-bromobut-2-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-di(2-chlorophenyl)(1-isopropenyl)borane;

[1-(2-ethoxypropyl)imidazole]-di(2-methoxyphenyl)(3chloroallyl)borane;

[1-(3-isopropylpropoxy)imidazole]-di(4-t-butylthiophenyl)(3-bromobut-2-enyl)borane;

[(2-benzyl)imidazole]-di(3-trifluoromethylphenyl)isopropenylborane;

[2-(4-bromobenzyl)imidazole]-di(2-methylphenyl)hex-3enylborane;

[2-(3-ethylbenzyl)imidazole]-di(3-isopropylphenyl)(3-chloroallyl)borane;

[2-(2-bromobenzyl)imidazole]-di(4-fluorophenyl)(3-bromobut2-enyl)borane;

[2-(2,4-dichlorobenzyl)imidazole]-di(2-chlorophenyl)(1-isopropenyl)borane;

[2,(3-fluoro-5-ethylbenzyl)imidazole]-di(2-fluorophenyl)hex3-enylborane;

[2-(2-chloro-3-iodobenzyl)imidazole]-di(2-methoxyphenyl)(3-chloroallyl)borane;

[5-(4-methylpentyl)imidazole]-di(4-t-butylthiophenyl)(3-bromobut-2-enyl)borane;

(5-t-butylimidazole)-di(3-trifluoromethylphenyl)isopropenylborane;

(5-ethylimidazole)-di(2-methylphenyl)hex-3-enylborane;

(5-methylimidazole)-di(3-isopropylphenyl)(3-chloroallyl)borane;

(5-isopropylimidazole)-di(4-fluorophenyl)(3-bromobut-2-enyl)borane;

(5-ethylimidazole)-di(2-chlorophenyl)isopropenylborane;

(5-t-butylimidazole)-di(2-methoxyphenyl)(3-chloroallyl)borane;

(1-ethyl-2-isopropylimidazole)-diphenylhex-3-enylborane;

(1-isopropyl-2-methylimidazole)-diphenyl(3-chloroallyl)borane;

(1-butyl-2-phenylimidazole)-diphenyl(3-bromobut-2-enyl)borane;

(1,2-diphenylimidazole)-diphenyl(3-methylbut-4-enyl)borane;

(1-octyl-2-phenylimidazole)-diphenyl(1-isopropenyl)borane;

(1-decyl-2-phenylimidazole)-diphenylhex-3-enylborane;

(1-dodecyl-2-phenylimidazole)-diphenyl(3-chloroallyl)borane;

[1-(2-ethyl-4,6-dimethylheptyl)-2-phenylimidazole]-diphenyl(3-bromobutenyl)borane;

(1-cyclopropyl-2-phenylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

(1-cyanomethyl-2-phenylimidazole)-diphenylisopropenylborane;

[1-(2-cyanopropyl)-2-phenylimidazole]-diphenylhex-3-enylborane;

[1-(4-cyanobutyl)-2-phenylimidazole]-diphenyl(3-chloroallyl)borane;

(1-methoxymethyl-2-phenylimidazole)-diphenyl(3-bromobut-2-enyl)borane;

(1-phenyl-2-phenylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

[2-p-chlorobenzyl-1-(2-phenylethyl)imidazole]-diphenyl(1isopropenyl)borane;

[1-(4-bromophenyl)-2-(2,6-dimethylbenzylimidazole]-diphenylhex-3-enylborane;

[1-(2-chlorophenyl)-5-methylimidazole]-diphenyl(3-chloroallyl)borane;

[1-(4-hexylphenyl)-5-methylimidazole]-diphenyl(3-bromo-2-enyl)borane;

[1-(2,6-dimethylphenyl)-5-methylimidazole]-diphenyl(3-methylbut-1-enyl)borane;

[1-(2-chloro-4-fluorophenyl)-5-methylimidazole]-diphenyl(1isopropenyl)borane;

[1-(4-fluoro-2-methylphenyl)-5-methylimidazole]-diphenylhex-3-enylborane;

[1-(3-chloroallyl)-5-methylimidazole]-diphenyl(3-chloroallyl)borane;

(1-ethyl-5-isopropylimidazole)-diphenyl(3-chloroallyl)borane;

(5-ethyl-1-vinylimidazole)-diphenyl(3-chloroallyl)borane;

[1-(2-fluoropent-2-enyl)-5-phenylimidazole]-diphenyl(3-bromobut-2-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]-5-phenylimidazole]-diphenyl(3-methylbut-1-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-5-phenylimidazole]-diphenylisopropenylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-5-phenylimidazole]-diphenylhex-3-enylborane;

[1-(2-ethoxypropyl)-5-phenylimidazole]-diphenyl(3-chloroallyl)borane;

[1-(3-isopropoxypropyl)-5-phenylimidazole]-diphenyl(3-bromobut-2-enyl)borane;

[1-(2-phenylethyl)-5-phenylimidazole]-3-methylbut-1-enyl)borane;

(2-benzyl-5-methylimidazole)-diphenylisopropenylborane;

[2-(4-bromobenzyl)-5-methylimidazole]-diphenylhex-3-enylborane;

[(2-ethylbenzyl)-5-methylimidazole]-diphenyl(3-chloroallyl)borane;

[2-(2-bromobenzyl)-5-methylimidazole]-diphenyl(3-bromobut-2-enyl)borane;

[2-(2,6-dimethylbenzyl)-5-methylimidazole]-diphenyl(3-methylbut-1-enyl)borane;

[2-(2,4-dichlorobenzyl)-5-methylimidazole]-diphenylisopropenylborane;

[2-(3-fluoro-5-ethylbenzyl)-5-methylimidazole]-diphenylhex-3-enylborane;

[2-(2-chloro-3-iodobenzyl)-5-methylimidazole]-diphenyl(3-chloroallyl)borane;

[4,5-di(4-methylpentyl)-imidazole]-diphenyl(3-bromobut-2-enyl)borane;

(4,5-dipropylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

(4,5-diisopropylimidazole)-diphenylisopropenylborane;

(4,5-dipentylimidazole)-diphenylhex-3-enylborane;

(5-methylimidazole)-diphenyl(3-chloroallyl)borane;

(4,5-dimethylimidazole)-diphenyl(3-bromobut-2-enyl)borane;

(4,5-dihexylimidazole)-diphenyl(3-methylbut-1-enyl)borane;

[4,5-diethylimidazole)-diphenylisopropenylborane;

(4,5-diisopropylimidazole)-diphenylhex-3-enylborane;

(5-t-butylimidazole-diphenyl(3-chloroallyl)borane;

(1-octyl-5-methylimidazole)-di(2-chlorophenyl)isopropenylborane;

(1-dodecyl-5-methylimidazole)-di(2-methoxyphenyl)(3-chloroallyl)borane;

(1-ethyl-4,6-dimethylheptyl-5-methylimidazole)-di(2-t-butylthiophenyl)(3-bromobut-2-enyl)borane;

(1-cyanomethyl-5-propylimidazole)-di(3-trifluoromethylphenyl)(1-isopropenyl)borane;

[1-(2-cyanopropyl)-5-propylimidazole]-di(2-methylphenyl)hex-3-enylborane;

[1-(4-cyanobutyl)-5-propylimidazole]-di(3-isopropylphenyl)-(3-chloroallyl)borane;

(1-methoxymethyl-5-propylimidazole)-di(4-fluorophenyl)(3-bromobut-2-enyl)borane;

[1-(2-phenylethyl)-5-propylimidazole]-di(2-chlorophenyl)isopropenylborane;

[1-(2-chlorophenyl)-5-β-phenylethylimidazole]-di(2-methoxyphenyl)(3-chloroallyl)borane;

[1-(4-hexylphenyl)-5-pentylimidazole]-di(4-t-butylthiophenyl)(3-bromobut-2-enyl)borane;

[1-(2-chloro-4-fluorophenyl)-5-hexylimidazole]-di(3-trifluoromethylphenyl)isopropenylborane;

[1-(1-fluoro-2-methylphenyl)-5-hexylimidazole]-di(2-methylphenyl)hex-3-enylborane;

[1-(3-chloroallyl)-5-hexylimidazole]-di(3-isopropylphenyl)(3-chloroallyl)borane;

[1-(2-fluoropent-2-enyl)-5-hexylimidazole]-di(4-fluorophenyl)(3-bromobut-2-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]-5-hexylimidazole]-di(2-chlorophenyl)(1-isopropenyl)borane;

[1-(2-ethoxypropyl)-5-(3-phenylpentyl)imidazole]-di(2methoxyphenyl)(3-chloroallyl)borane;

[1-(3-isopropoxypropyl)-5-(2-pentyl)imidazole]-di(4-t-butylthiophenyl)(3-bromobut-2-enyl)borane;

(2-benzyl-5-methylimidazole)-di(3-trifluoromethylphenyl)isopropenylborane;

[2-(4-bromobenzyl)-5-methylimidazole]-di(2-methylphenyl)-hex-3-enylborane;

[2-(3-ethylbenzyl)-5-methylimidazole]-di(3-isopropylphenyl)(3-chloroallyl)borane;

[2-(2-bromobenzyl)-5-methylimidazole]-di(4-fluorophenyl)(3-bromobut-2-enyl)borane;

[2-(2,4-dichlorobenzyl)-5-methylimidazole]-di(2-chlorophenyl)(1-isopropenyl)borane;

[2-(3-fluoro-5-ethylbenzyl)-5-methylimidazole]-di(2-fluorophenyl)hex-3-enylborane;

[2-(2-chloro-3-iodobenzyl)-5-methylimidazole]-di(2-methoxyphenyl)(3-chloroallyl)borane;

(4,5-dimethylimidazole)-di(3-trifluoromethylphenyl)isopropenylborane;

(4,5-diisopropylimidazole)-di(2-methylphenyl)hex-3-enylborane;

imidazole-phenyl(p-tolyl)hex-3-enylborane;

imidazole-(2-ethylphenyl)phenyl(3-chloroallyl)borane;

(1-methoxymethylimidazole)-(4-butyoxyphenyl)phenyl(3-bromobut-2-enyl)borane;

[1-(2-fluoropent-2-enyl)imidazole]-(3-fluorophenyl)phenyl(3-bromobut-2-enyl)borane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-(2-methylthiophenyl)phenylisopropenylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylhex-3-enylborane;

[1-(2-ethoxypropyl)imidazole]-(3-trifluoromethylphenyl)phenyl(3-chloroallyl)borane;

(2-benzylimidazole)-(4-methylphenyl)phenylisopropenylborane;

(2-ethylbenzyl)imidazole-(3-methoxyphenyl)phenyl(3-chloroallyl)borane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-(2-ethylthiophenyl)-phenylhex-3-enylborane;

[5-(4-methylphentyl)imidazole]-(4-ethylphenyl)phenyl(3-bromobut-2-enyl)borane;

(5-isopropylimidazole)-phenyl(σ-tolyl)(3-methylbut-1-enyl)borane;

imidazole-(2-methylphenyl)(3-chlorophenyl)hex-3-enylborane;

imidazole-(3-isopropylphenyl)(2-t-butoxyphenyl)(3-chloroallyl)borane;

(1-cyanomethylimidazole)-(2-fluorophenyl)(3-trifluoromethylphenyl)(1-isopropenyl)borane;

(1-methoxymethylimidazole)-(4-fluorophenyl)(4-propylthiophenyl)(3-bromobut-2-enyl)borane;

[1-(2-phenylethylimidazole)-(2-chlorophenyl)(3-trifluoromethylphenyl)isopropenylborane;

[(2-benzyl)imidazole]-(4-butylphenyl)(3-trifluoromethylphenyl)isopropenylborane;

[2,(3-fluoro-5-ethylbenzyl)imidazole]-(2-fluorophenyl)(3-methoxyphenyl)hex-3-enylborane;

[5-(4-methylpentyl)imidazole]-(4-butylphenyl)(4-t-butylthiophenyl)(3-bromobut-2-enyl)borane;

(1-ethyl-2-isopropylimidazole)-phenyl(m-tolyl)hex-3-enylborane;

(1-isopropyl-2-methylimidazole)-(4-fluorophenyl)phenyl(3-chloroallyl)borane;

[1-(2-ethyl-4,6-dimethylheptyl)-2-phenylimidazole]-(3-isopropylthiophenyl)phenyl(3-bromobutenyl)borane;

(1-cyclopropyl-2-phenylimidazole)-(4-2',2'-dibromoethylphenyl)phenyl(3-methylbut-1-enyl)borane;

[1-(2-chlorophenyl)-5-methylimidazole]-phenyl(p-tolyl)-(3-chloroallyl)borane;

[1-(3-chloroallyl)-5-methylimidazole]-(2-trifluoromethylphenyl)phenyl(3-chloroallyl)borane;

(2-benzyl-5-methylimidazole)-(2-ethylphenyl)phenylisopropenylborane;

[(2-ethylbenzyl)-5-methylimidazole]-(4-butoxyphenyl)phenyl(3-chloroallyl)borane;

(4,5-propylimidazole)-(4-fluorophenyl)phenyl(3-methylbut-1-enyl)borane;

(1-dodecyl-5-methylimidazole)-(2-methoxyphenyl)(4-t-butylthiophenyl)(3-chloroallyl)borane;

(2-benzyl-5-methylimidazole)-(4-propylphenyl)(3-trifluoromethylphenyl)isopropenylborane;

[2-(4-bromobenzyl)-5-methylimidazole]-(3-fluorophenyl)(2-methylphenyl)hex-3-enylborane;

(4,5-methylimidazole)-(4-isopropylthiophenyl)(3-trifluoromethylphenyl)isopropenylborane;and

(5-ethyl-4-isopropylimidazole)-(2-methylphenyl)(2-methoxyphenyl)hex-3-enylborane.

EXAMPLE 4 Imidazole-Diphenylmethylborane ##STR15##

In this example, 1.23 g (6.2 mmol) of diphenylmethylboronammonia complexis added to 50 mL of chloroform at room temperature followed by theaddition of 0.42 g (6.2 mmol) of imidazole. The resulting mixture washeated at reflux for four hours. After cooling in an ice bath, a whitesolid precipitated which was collected by filtration and washed withcold chloroform. The white solid is dried in vacuo, 1.15 g (83% yield),m.p. 154°-156° C.

Similarly, by following the same general procedure using the appropriatestarting materials, the following compounds can be prepared:

(1-hydroxymethylimidazole)-diphenylethylborane;

[1-(5-hydroxypentylimidazole)]-diphenylmethylborane;

[1-(4-hydroxyhexylimidazole)]-diphenylisopropylborane;

imidazole-diphenylethylborane;

imidazole-diphenylbutylborane;

imidazole-diphenylisopropylborane;

imidazole-diphenylcyclohexylborane;

(1-octylimidazole)-diphenylmethylborane;

(1-decylimidazole)-diphenylethylborane;

(1-dodecylimidazole)-diphenylbutylborane;

[1-(2-ethyl-4,6-dimethyl)heptylimidazole]-diphenylisopropyl borane;

(1-cyclopropylimidazole)-diphenylcyclohexylborane;

(1-cyanomethylimidazole)-diphenylmethylborane;

[1-(2-cyanopropyl)imidazole]-diphenylethylborane;

[1-(4-cyanobutyl)imidazole]-diphenylbutylborane;

(1-methoxymethylimidazole-diphenylisopropylborane;

(1-phenylimidazole)-diphenyloyolohexylborane;

[1-(2-phenylethyl)imidazole]-diphenylmethylborane;

[1-(4-bromophenyl)imidazole]-diphenylethylborane;

[1-(2-chlorophenyl)imidazole]-diphenylisopropylborane;

[1-(4-hexylphenyl)imidazole-diphenylcyclohexylborane;

[1-(2,6-dimethylphenyl)imidazole-diphenylmethylborane;

[1-(2-chloro-4-fluorophenyl)imidazole]-diphenylethylborane;

[1-(4-fluoro-2-methylphenyl)imidazole-diphenylbutylborane;

[1-(3-chloroallyl)imidazole-diphenylisopropylborane;

[1-(2-fluoropent-2-enyl)imidazole]-diphenylcyclohexylborane;

(1-[2-(1,3-dioxolan-2-yl)ethyl]imidazole)-diphenylmethylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole-diphenylethylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-diphenylbutylborane;

[1-(2-ethoxypropyl)imidazole]-diphenylisopropylborane;

(2-phenylimidazole)-diphenyl(fluoromethyl)borane;

(2-benzylimidazole)-diphenyl(1,2-dichloroethyl)borane;

[2-(4-bromobenzyl)imidazole]-diphenylbutylborane;

[2-(3-ethylbenzyl)imidazole]-diphenylisopropylborane;

[2-(2-bromobenzyl)imidazole]-diphenylcyclohexylborane;

[2-(2,6-dimethylbenzyl)imidazole]-diphenyl(trifluoro)borane;

[2-(2,4-dichlorobenzyl)imidazole]-diphenylethylborane;

[2-(3-fluoro-5-ethylbenzyl)imidazole]-diphenyl(3-chloro-4-fluorobutyl)borane;

[2-(2-chloro-3-iodobenzyl)imidazole]-diphenylcyclohexylborane;

[5-(4-methylpentyl)imidazole]-diphenylmethylborane;

(5-isopropylimidazole)-diphenylethylborane;

(5-t-butylimidazole)-diphenylbutylborane;

(5-ethylimidazole)-diphenylisopropylborane;

(5-methylimidazole)-diphenylcyclohexylborane;

(5-isopropylimidazole)-diphenylmethylborane;

(5-hexylimidazole)-diphenylethylborane;

(5-ethylimidazole)-diphenylbutylborane;

(5-isopropylimidazole)-diphenylisopropylborane;

(5-t-butylimidazole)-diphenylcyclohexylborane;

imidazole-di(2-methylphenyl)ethylborane;

imidazole-di(3-isopropylphenyl)butylborane;

imidazole-di(4-fluoropentyl)isopropylborane;

(1-octylimidazole)-di(2-chlorophenyl)methylborane;

(1-dodecylimidazole)-di(2-methoxyphenyl)butylborane;

[1-(2-ethyl-4,6-dimethylheptyl)imidazole]-di(4-t-butylthiophenyl)isopropylborane;

(1-cyanomethylimidazole)-di(3-trifluoromethylphenyl)methylborane;

[1-(2-cyanopropyl)imidazole]-di(2-methylphenyl)ethylborane;

[1-(4-cyanobutyl)imidazole]-di(3-isopropylphenyl)butylborane;

(1-methoxymethylimidazole)-di(4-fluorophenyl)isopropylborane;

[1-(2-phenylethyl)imidazole]-di(2-chlorophenyl)methylborane;

[1-(4-bromophenyl)imidazole]-di(3-fluorophenyl)ethylborane;

[1-(2-chlorophenyl)imidazole]-di(2-methoxyphenyl)isopropylborane;

[1-(4-hexylphenyl)imidazole]-di(4-t-butylthiophenyl)cyclohexylborane;

[1-(2-chloro-4-fluorophenyl)imidazole]-di(3-trifluoromethylphenyl)ethylborane;

[1-4-fluoro-2-methylphenyl)imidazole]-di(2-methylphenyl)butylborane;

[1-(3-chloroallyl)imidazole]-di(isopropylphenyl)isopropylborane;

[1-(2-fluoropent-2-enyl)imidazole]-di(2-fluorophenyl)cyclohexylborane;

(1-[2-(1,3-dioxolan-2-yl)butyl]imidazole)-di(2-chlorophenyl)ethylborane;

[1-(2-ethoxypropyl)imidazole]-di(2-methoxyphenyl)isopropylborane;

[1-(3-isopropylpropoxy)imidazole]-di(4-butylthiophenyl)cyclohexylborane;

(2-benzylimidazole)-di(3-trifluoromethylphenyl)ethylborane;

[2-(4-bromobenzyl)imidazole]-di(2-methylphenyl)butylborane;

[2-(3-ethylbenzyl)imidazole]-di(3-isopropylphenyl)isopropylborane;

[2-(2-bromobenzyl)imidazole]-di(4-fluorophenyl)cyclohexylborane;

[2-(2,4-dichlorobenzyl)imidazole]-di(2-chlorophenyl)ethylborane;

[2-(2-chloro-3-iodobenzyl)imidazole-di(2-methoxyphenylcyclohexylborane;

[5-(4-methylpentyl)imidazole]-di(4-t-butylthiophenyl)methylborane;

(5-t-butylimidazole)-di(2-methylphenyl)butylborane;

(5-ethylimidazole)-di(3-trifluoromethylphenyl)ethylborane;

(5-methylimidazole)-di(3-isopropylphenyl)cyclohexylborane;

(5-isopropylimidazole-di(4-fluorophenyl)methylborane;

(5-ethylimidazole)-di(2-chlorophenyl)isopropylborane;

(5-t-butylimidazole)-di(2-methoxyphenyl)cyclohexylborane;

(1-hydroxymethylimidazole-(4-isopropylphenyl)phenylethylborane;

imidazole-(2-methoxyphenyl)phenylisopropylborane;

(2-phenylimidazole)-(3-fluorophenyl)phenylmethylborane;

(5-isopropylimidazole)-(4-ethylthiophenyl)phenyl(2,2-fluoroethyl)borane;

imidazole-(3-isopropylphenyl)(2-trifluoromethylphenyl)butylborane;

(1-cyanomethylimidazole)-(4-propylphenyl)(3-trifluoromethylphenyl)methylborane;and

(5-t-butylimidazole)-(2-methylthiophenyl)(2-methoxyphenyl)cyclohexylborane.

EXAMPLE 5 (1-Isopropenylimidazole)-Diphenylmethylborane ##STR16##

In this example, 1.39 g (7 03 mmol) of diphenylmethylboronammoniacomplex, 760 milligrams (7.03 mmol) of 1-isopropenylimidazole, and 50 mLof chloroform are stirred at room temperature for one hour. Thechloroform is removed by evaporation under reduced pressure and theresultant white solid triturated overnight with 25 mL of methanol. Thecrystals are collected by suction filtration and dried in vacuo toprovide 1.9 g of the title compound, m.p. 172°-174° C.

EXAMPLE 6

Similarly, by applying the same general procedures using the appropriatestarting materials, the compounds identified in Table A below areprepared:

                                      TABLE A                                     __________________________________________________________________________     ##STR17##                                                                                                                         Melting                  No. R         R.sup.1   R.sup.2 R.sup.3                                                                          R.sup.4 X    Y    Point                    __________________________________________________________________________                                                         °C.               1   CH.sub.3  H         H       H  H       H    H    154-156                  2   CH.sub.3  H         H       H  H       4-CH.sub.3                                                                         4-CH.sub.3                                                                         141-144                  3   CH.sub.3  H         H       H  H       4-Cl 4-Cl oil                      4   CH.sub.3  H         CH.sub.3                                                                              H  H       H    H    163-166                  5   CH.sub.3  CH.sub.3  H       H  H       H    H    124-126                  6   CH.sub.3  H         H       H  CH.sub.3                                                                              H    H    163-165                  7   CH.sub.3  CH.sub.3  H       H  H       4-CH.sub.3                                                                         4-CH.sub.3                                                                         135-136                  8   CH.sub.3  H         CH.sub.3                                                                              H  H       4-Cl 4-Cl oil                      9   CH.sub.3  CH.sub.3  H       H  H       4-Cl 4-Cl oil                      10  CH.sub.3  H         CH.sub.3                                                                              H  H       4-F  4-F  oil                      11  CH.sub.3  CH.sub.3  H       H  H       4-F  4-F  111-113                  12  CH.sub.3  H         H       H  CH.sub.3                                                                              4-F  4-F  174-175                  13  CH.sub.3  CH.sub.3  H       H  H       4-CF.sub.3                                                                         4-CF.sub.3                                                                         100-102                  14  CH.sub.3  H         CH.sub.3                                                                              H  H       4-OCH.sub.3                                                                        4-OCH.sub.3                                                                        oil                      15  CH.sub.3  CH.sub.3  H       H  H       4-OCH.sub.3                                                                        4-OCH.sub.3                                                                        oil                      16  CH.sub.3  CH.sub.3  H       H  H       4-SCH.sub.3                                                                        4-SCH.sub.3                                                                        108-112                  17  CH.sub.3  H         C.sub.2 H.sub.5                                                                       H  H       H    H    102-104                  18  CH.sub.3  C.sub.2 H.sub.5                                                                         H       H  H       H    H    oil                      19  CH.sub.3  H         C.sub.2 H.sub.5                                                                       H  H       4-OCH.sub.3                                                                        4-OCH.sub.3                                                                        oil                      20  CH.sub.3  CH.sub.2 CH.sub.2 CH.sub.3                                                              H       H  H       H    H    oil                      21  CH.sub.3  CH.sub.2 CH.sub.2 CH.sub.3                                                              H       H  H       4-Cl 4-Cl oil                      22  CH.sub.3  CH.sub. 2 CH.sub.2 CH.sub.3                                                             H       H  H       4-CF.sub.3                                                                         4-CF.sub.3                                                                         oil                      23  CH.sub.3  H         H       H  CH.sub.2 CH.sub.2 CH.sub.3                                                            H    H    oil                      24  CH.sub.3  CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    180-182                  25  CH.sub.3  (CH.sub.2).sub.3 CH.sub.3                                                               H       H  H       H    H    oil                      26  CH.sub.3  CH.sub.2 CH(CH.sub.3).sub.2                                                             H       H  H       H    H    oil                      27  CH.sub.3  H         H       H  CH(CH.sub.3).sub.2                                                                    H    H    165-166                  28  CH.sub.3  H         H       H  C(CH.sub.3).sub.3                                                                     H    H    205-206                  29  CH.sub.3  (CH.sub.2).sub.4 CH.sub.3                                                               H       H  H       H    H    94-95                    30  CH.sub.3  (CH.sub.2).sub.9 CH.sub.3                                                               H       H  H       H    H    oil                      31  CH.sub.3  (CH.sub.2).sub.2 CH.sub.3                                                               CH.sub.3                                                                              H  H       H    H    solid 58-62                                                                   (decomposes)             32  CH.sub.3  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                              H  H       H    H    130-132                  33  CH.sub.3  (CH.sub.2).sub.3 CH.sub.3                                                               CH.sub.3                                                                              H  H       H    H    98-99                    34  CH.sub.3  (CH.sub.2).sub.2 CH.sub.3                                                               C.sub.2 H.sub.5                                                                       H  H       H    H    119-120                  35  CH.sub.3  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                       H  H       H    H    99-100                   36  CH.sub.3  CH.sub.3  (CH.sub.2).sub.3 CH.sub.3                                                             H  H       H    H    oil                      37  CH.sub.3  Cyclopentyl                                                                             H       H  H       H    H    182-183                  38  CH.sub.3  CHCH.sub.2                                                                              H       H  H       H    H    167-170                  39  CH.sub.3  CH.sub.2 CHCH.sub.2                                                                     H       H  H       H    H    115-116                  40  CH.sub.3  CHCH.sub.2                                                                              (CH.sub.2).sub.2 CH.sub.3                                                             H  H       H    H    oil                      41  CH.sub.3  CHCH.sub.2                                                                              CH.sub.3                                                                              H  H       H    H    oil                      42  CH.sub.3  (CH.sub.2).sub.2 CH.sub.2 Cl                                                            H       H  H       H    H    110-113                  43  CH.sub.3  CH.sub.2 CF.sub.3                                                                       H       H  H       H    H    182-184                  44  CH.sub.3  CH.sub.2 CHCHCl                                                                         H       H  H       H    H    113-115-90%                                                                    ##STR18##               45  CH.sub.3  CH.sub.2 C(Br)CH.sub.2                                                                  H       H  H       H    H    145-146                  46  CH.sub.3  CH.sub.2 CHCCl.sub.2                                                                    H       H  H       H    H    oil                      47  CH.sub.3  CH.sub.2 CN                                                                             H       H  H       H    H    184-186                  48  CH.sub.3  CH.sub.2 OCH.sub.3                                                                      H       H  H       H    H    oil                      49  CH.sub.3  H         H       H  φ*  H    H    120-124                  50  CH.sub.3  CH.sub.2 φ                                                                          H       H  H       H         98-104                   51  CH.sub.3  CH.sub.2 -4-Brφ                                                                     H       H  H       H    H    125-129                  52  Cyclopropyl                                                                             H         CH.sub.3                                                                              H  H       H    H    oil                      53  Cyclopropyl                                                                             CH.sub.3  H       H  H       H    H    140-142                  54  Cyclopropyl                                                                             H         H       H  CH.sub.3                                                                              H    H    oil                      55  Cyclopropyl                                                                             C.sub.2 H.sub.5                                                                         H       H  H       H    H    160-162                  56  Cyclopropyl                                                                             (CH.sub.2).sub.2 CH.sub.3                                                               H       H  H       H    H    oil                      57  Cyclopropyl                                                                             CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    166-167                  58  Cyclopropyl                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                             H       H  H       H    H    130-132                  59  Cyclopropyl                                                                             CHCH.sub.2                                                                              H       H  H       H    H    oil                      60  Cyclopropyl                                                                             CH.sub.2 CHCH.sub.2                                                                     H       H  H       H    H    oil                      61  Cyclopropyl                                                                             **        H       H  H       H    H    120-121                  62  Cyclopentyl                                                                             CH.sub.3  H       H  H       H    H    120-124                  63  Cyclopentyl                                                                             (CH.sub.2).sub.2 CH.sub.3                                                               H       H  H       H    H    112-115                  64  Cyclopentyl                                                                             CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    112-114                  65  Cyclopentyl                                                                             Cyclopentyl                                                                             H       H  H       H    H    103-104                  66  Cyclopentyl                                                                             CHCH.sub.2                                                                              H       H  H       H    H    oil                      67  Cyclopentyl                                                                             CH.sub.2 φ                                                                          H       H  H       H    H    122-124                  68  Cyclopentyl                                                                             **        H       H  H       H    H    133-135                  69  Cyclohexyl                                                                              CH.sub.3  H       H  H       H    H    141-142                  70  Cyclohexyl                                                                              (CH.sub.2).sub.2 CH.sub.3                                                               H       H  H       H    H    134-136                  71  Cyclohexyl                                                                              CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    125-128                  72  Cyclohexyl                                                                              **        H       H  H       H    H    145-149                  73  CHCH.sub.2                                                                              H         H       H  H       H    H    128-131                  74  CHCH.sub.2                                                                              H         H       H  H       4-Cl 4-Cl oil                      75  CHCH.sub.2                                                                              H         H       H  H       4-CF.sub.3                                                                         4-CF.sub.3                                                                         oil                      76  CHCH.sub.2                                                                              H         CH.sub.3                                                                              H  H       H    H    oil                      77  CHCH.sub.2                                                                              CH.sub.3  H       H  H       H    H    132-133                  78  CHCH.sub.2                                                                              H         H       H  CH.sub.3                                                                              H    H    oil                      79  CHCH.sub.2                                                                              H         CH.sub.3                                                                              H  H       H    H    oil                      80  CHCH.sub.2                                                                              CH.sub.3  H       H  H       4-CH.sub.3                                                                         4-CH.sub.3                                                                         oil                      81  CHCH.sub.2                                                                              H         CH.sub.3                                                                              H  H       4-CH.sub.3                                                                         4-CH.sub.3                                                                         oil                      82  CHCH.sub.2                                                                              H         CH.sub.3                                                                              H  H       4-F  4-F  oil                      83  CH.sub.2CH.sub.2                                                                        CH.sub.3  H       H  H       4-F  4-F  80-83                    84  CH.sub.2CH.sub.2                                                                        H         CH.sub.3                                                                              H  H       4-Cl 4-Cl oil                      85  CHCH.sub.2                                                                              CH.sub.3  H       H  H       4-Cl 4-Cl oil                      86  CHCH.sub.2                                                                              CH.sub.3  H       H  H       4-SCH.sub.3                                                                        4-SCH.sub.3                                                                        oil                      87  CHCH.sub.2                                                                              H         C.sub.2 H.sub.5                                                                       H  H       H    H    oil                      88  CHCH.sub.2                                                                              C.sub.2 H.sub.5                                                                         H       H  H       H    H    oil                      89  CHCH.sub.2                                                                              (CH.sub.2)CH.sub.3                                                                      H       H  H       H    H    oil                      90  CHCH.sub.2                                                                              H         H       H  (CH.sub.2).sub.2 CH.sub.3                                                             H    H    oil                      91  CHCH.sub.2                                                                              CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    150-151                  92  CHCH.sub.2                                                                              (CH.sub.2).sub.3 CH.sub.3                                                               H       H  H       H    H    oil                      93  CHCH.sub.2                                                                              H         CH.sub.2 CH(CH.sub.3).sub. 2                                                          H  H       H    H    oil                      94  CHCH.sub.2                                                                              H         C(CH.sub.3).sub.3                                                                     H  H       H    H    204-206                  95  CHCH.sub.2                                                                              (CH.sub.2).sub.4 CH.sub.3                                                               H       H  H       H    H    78-79                    96  CHCH.sub.2                                                                              (CH.sub.2).sub.9 CH.sub.3                                                               H       H  H       H    H    oil                      97  CHCH.sub.2                                                                              Cyclopentyl                                                                             H       H  H       H    H    158-160                  98  CHCH.sub.2                                                                              CH.sub.2 CF.sub.3                                                                       H       H  H       H    H    151-153                  99  CHCH.sub.2                                                                              CHCH.sub.2                                                                              H       H  H       H    H    153-156                  100 CHCH.sub.2                                                                              CH.sub.2 CHCHCH.sub.3                                                                   H       H  H       H    H    103-105-85%                                                                    ##STR19##               101 CHCH.sub.2                                                                              CH.sub.2 C(Br)CH.sub.2                                                                  H       H  H       H    H    oil                      102 CHCH.sub.2                                                                              CH.sub.2 CHCHCl                                                                         H       H  H       H    H    104-106-90%                                                                    ##STR20##               103 CHCH.sub.2                                                                              CH.sub.2 CHCCl.sub.2                                                                    H       H  H       H    H    oil                      104 CHCH.sub.2                                                                              CH.sub.2 φ                                                                          H       H  H       H    H    120-123                  105 CHCH.sub.2                                                                              H         H       H  φ   H    H    181-183                  106 CHCH.sub.2                                                                              CH.sub.2 (4-Brφ)                                                                    H       H  H       H    H    oil                      107 CHCH.sub.2                                                                              **        H       H  H       H    H    oil                      108 CHCH.sub.2                                                                              CH.sub.3  CH.sub.3                                                                              H  H       H    H    oil                      109 CHCH.sub.2                                                                              CH.sub.2 CH.sub.3                                                                       CH.sub.3                                                                              H  H       H    H    oil                      110 CHCH.sub.2                                                                              CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                              H  H       H    H    118-120                  111 CHCH.sub.2                                                                              (CH.sub.2).sub.3 CH.sub.3                                                               CH.sub.3                                                                              H  H       H    H    61-62                    112 CHCH.sub.2                                                                              (CH.sub.2).sub.2 CH.sub.3                                                               C.sub.2 H.sub.5                                                                       H  H       H    H    101-102                  113 CHCH.sub.2                                                                              CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                       H  H       H    H    oil                      114 CHCH.sub.2                                                                              CH.sub.3  (CH.sub.2).sub.11 CH.sub.3                                                            H  H       H    H    oil                      115 CHCH.sub.2                                                                              CHCH.sub.2                                                                              CH.sub.3                                                                              H  H       H    H    oil                      116 CHCH.sub.2                                                                              CHCH.sub.2                                                                              (CH.sub.2).sub.2 CH.sub.3                                                             H  H       H    H    147-150                  117 CH.sub.2 CHCH.sub.3                                                                     CH.sub.3  H       H  H       H    H    114-115                  118 CH.sub.2 CHC(CH.sub.3).sub.2                                                            H         H       H  H       H    H    oil                      119 CH.sub.3  CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           H       H  H       H    H    143-145                  120 CH.sub.2 CH.sub.3                                                                       CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    135-137                  121 CH.sub.2 CH.sub.2 CH.sub.3                                                              CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    122-123                  122 (CH.sub.2).sub.3 CH.sub.3                                                               CH(CH.sub.3).sub.2                                                                      H       H  H       H    H    80-82                    123 CH.sub.3  CH(CH.sub.3)CH.sub.2                                                                    H       H  H       H    H    172-174                  124 CH.sub.3  CH.sub.2 C(O)OCH.sub.3                                                                  H       H  H       H    H    139-140                  125 CH.sub.3  CH.sub.2 (4-NO.sub.2 φ)                                                             H       H  H       H    H    159-162                  126 CHCH.sub.2                                                                              CH(CH.sub.3)CH.sub.2 CH.sub.3                                                           H       H  H       H    H    114-115                  127 CHCH.sub.2                                                                              CH(CH.sub.3)CH.sub.2                                                                    H       H  H       H    H    149                      128 CHCH.sub.2                                                                              CH.sub.2 CH.sub.2 OH                                                                    H       H  H       H    H    Oil                      129 CHCH.sub.2                                                                              CH.sub.2 C(O)OCH.sub.3                                                                  H       H  H       H    H    149-151                  130 CHCH.sub.2                                                                              CH.sub.2 (4-NO.sub.2 φ)                                                             H       H  H       H    H    141-144                  131 CH.sub.3  C(CH.sub.3).sub.3                                                                       H       H  H       H    H    188-194                  132 CHCH.sub.2                                                                              C(CH.sub.3).sub.3                                                                       H       H  H       H    H    174-178                  133 CH.sub.3  Cyclopropyl                                                                             H       H  H       H    H    171-173                  134 CHCH.sub.2                                                                              Cyclopropyl                                                                             H       H  H       H    H    159-161                  __________________________________________________________________________     * φ = Phenyl, for example, 4Brφ = 4-bromophenyl.                      ##STR21##                                                                

EXAMPLE 7

The compounds identified in Table A hereinabove were tested for thepreventative control of certain plant diseases by the proceduresdescribed below. The results of this testing is set forth in Table 1hereinbelow, wherein Compound Numbers refer to the Compound Numbersassigned the respective compounds in Table A.

Tomato Late Blight (TLB)

Compounds of the invention were tested for the preventative control ofthe Tomato Late Blight organism Phytophthora infestans. Three to sixweek old tomato (cultivar Bonny Best) seedlings were used. The tomatoplants were sprayed with either a 500 or 200 ppm suspension of the testcompound in acetone, water and a non-ionic emulsifier. The sprayedplants were then inoculated 1 day later with the organism, placed in anenvironmental chamber and incubated at 66° F. to 68° F. and 100%relative humidity for 16 to 24 hours. Following the incubation, theplants were maintained in a greenhouse for approximately 7 days. Thepercent disease control provided by a given test compound was based onthe percent disease reduction relative to untreated check plants.

The averaged results are reported in Table 1.

Rice Blast (RB)

Compounds of this invention were tested for control of the Rice Blastorganism Piricularia oryzae, using 10 to 14 day old rice plant seedlings(Calrose M-9 variety). Seedling plants were sprayed with a 500 or 200ppm solution of the test compound in acetone, water and a non-ionicemulsifier. The sprayed plants were inoculated 1 day later with theorganism in an environmental chamber. After inoculation, the plants werekept in an environmental chamber for about 48 hours under conditions ofabout 72° F. to 75° F. and about 100% relative humidity. Following theincubation period, the plants were placed in a greenhouse with atemperature of about 80° F. and maintained with bottom watering forabout 12 to 16 days. The percent disease control provided by a giventest compound is based on a comparison of the percentage diseaserelative to the percent disease development on untreated check plants.The averaged results are reported in Table 1.

Celery Late Blight (CLB)

The Celery Late Blight tests were conducted using celery (Utah) plants11 weeks old. The Celery Late Blight organism was Septoria apii. Thecelery plants were sprayed with either 500 or 200 ppm solutions of thetest compound mixed with acetone, water and a nonionic emulsifier. Theplants were then inoculated one day later with the organism and placedin an environmental chamber and incubated at 66° F. to 68° F. in 100%relative humidity for approximately 48 hours. Following the incubation,the plants were allowed to dry and then were maintained in a greenhousefor approximately 14 days. One plant was used per compound. Sixuntreated plants were used as the check for each screening group ofcompound. The percent disease control provided by a given candidatetoxicant is based on the percent disease reduction relative to untreatedcheck plants. The results are reported in Table 1.

Bean Powdery Mildew (BPM)

The compounds of the invention were tested for the control of the BeanPowdery Mildew organism, Erysiphe polygoni. Seedling bean plants weresprayed with a 500 or 200 ppm solution of the test compound in acetone,water and a nonionic emulsifier. The sprayed plants were then inoculated1 day later with the organism. The plants were maintained for 10 days attemperatures of 68° F. at night with daytime temperatures of 72° F. to80° F.; relative humidity was maintained at 40% to 60%. One plant wasused per compound. Six untreated plants were used as the check for eachscreening group of compounds. The percent disease control provided by agiven test compound was based on the percent disease reduction relativeto the untreated check plants. The results are reported in Table 1.

Bean Rust (BR)

The Leaf Rust test was made using pinto beans. The pathogen was Uromycesphaseoli tipica. The bean plants were sprayed with either a 500 or 200ppm solution of the test compound in an acetone-water mixture containinga nonionic emulsifier. The treated plants were inoculated thereafterwith the pathogen and then incubated in an environmental chamber forapproximately 20 hours at 100% relative humidity and a temperature of68° F. to 70° F. The plants were then removed from the chamber, allowedto dry, and then maintained in a greenhouse at a 60% to 80% relativehumidity. The amount of infection on the leaves was rated after about 14days. The percent disease control provided by a given test compound wasbased on the percent disease reduction relative to untreated checkplants. The results are reported in Table 1.

                  TABLE 1                                                         ______________________________________                                        Preventative Fungicidal Activity                                              (Dosage rate 200 ppm unless otherwise indicated)                              Percent Control                                                               COMPOUND NO. TLB     RB      CLB   BPM   BR                                   ______________________________________                                         1           0       94      98    0     0                                     2*          0       94      89    100   0                                     3*          0       0       98    100   0                                     4*          67      98      94    0     0                                     5*          0       94      100   100   100                                   6           0       100     100   95    0                                     7*          0       94      0     100   100                                   8*          18      0       100   95    100                                   9*          21      60      94    0     100                                  10           80      87      0     0     100                                   11*         55      94      100   100   100                                   12*         89      94      100   100   100                                  13           0       --      62    100   100                                  14           44      0       0     0     40                                   15           05      --      100   0     100                                  16           0       0       84    0     0                                    17           95      46      100   100   100                                  18           95      94      100   84    100                                  19           76      0       62    0     92                                   20           95      94      100   96    100                                  21           0       100     100   0     0                                    22           0       0       91    0     100                                  23           0       --      0     0     0                                    24           100     89      100   0     100                                  25           0       100     100   100   0                                    26           100     72      100   96    100                                  27           0       100     0     0     100                                  28           0       0       100   0     100                                  29           92      93      100   0     0                                    30           92      0       0     100   96                                   31           25      --      100   9     100                                  32           0       67      0     0     85                                   33           0       93      0     0     100                                  34           0       93      92    0     100                                  35           75      0       0     0     100                                  36           92      89      0     0     0                                    37           69      73      100   0     0                                     38*         --      58      94    0     --                                   39           74      0       0     0     100                                  40           75      48      0     95    100                                  41           0       48      0     0     100                                  42           75      90      100   0     100                                  43           100     91      0     100   100                                  44           100     0       100   100   100                                  45           0       0       100   0     100                                  46           100     0       100   0     100                                  47           72      100     100   0     100                                  48           0       0       100   0     100                                   49*         --      95      100   100   --                                    50*         57      98      94    100   100                                   51*         0       95      100   0     100                                  52           92      96      70    100   0                                    53           100     68      100   100   100                                  54           84      100     100   100   100                                  55           93      100     0     100   100                                  56           92      100     100   93    100                                  57           72      100     100   35    100                                  58           0       0       0     0     0                                    59           0       100     100   100   100                                  60           74      0       0     0     0                                    61           93      0       90    100   100                                  62           75      0       100   0     100                                  63           93      0       100   0     100                                  64           0       0       100   94    100                                  65           0       0       100   94    100                                  66           0       0       0     0     91                                   67           0       0       93    0     100                                  68           74      0       100   0     100                                  69           0       0       100   0     100                                  70           0       0       0     0     100                                  71           93      0       0     0     96                                   72           100     0       0     0     100                                   73*         0       98      100   0     0                                    74           0       0       59    0     100                                  75           0       --      75    0     100                                   76*         0       94      100   0     29                                    77*         98      94      100   49    100                                  78           74      100     73    100   100                                  79           0       --      100   0     100                                   80*         71      94      100   100   100                                   81*         86      98      89    0     100                                  82           0       75      86    0     92                                    83*         0       89      100   95    100                                  84           0       0       73    0     100                                  85           0       75      86    0     100                                  86           0       0       84    0     0                                    87           0       92      92    0     100                                  88           0       100     100   100   100                                  89           0       93      100   94    100                                  90           0       93      92    0     0                                    91           69      93      88    0     100                                  92           100     72      0     0     100                                  93           0       91      74    0     96                                   94           0       0       59    40    100                                  95           68      93      92    0     100                                  96           0       0       0     0     96                                   97           93      0       100   0     0                                    98           0       48      0     0     100                                  99           98      100     100   100   100                                  100          75      48      100   0     0                                    101          0       0       100   0     0                                    102          0       0       100   0     100                                  103          0       0       100   0     100                                  104*         78      89      94    83    100                                  105*         --      95      100   100   --                                   106*         0       89      94    100   100                                  107          0       --      94    100   100                                  108          0       0       100   0     100                                  109          0       --      91    0     100                                  110          90      100     0     0     0                                    111          0       100     100   0     0                                    112          0       100     0     100   100                                  113          65      100     0     0     100                                  114          0       --      100   0     100                                  115          0       0       100   0     100                                  116          75      48      0     95    100                                  117          0       0       0     0     0                                    118          93      0       0     0     0                                    119          100     93      100   0     0                                    120          69      --      100   0     100                                  121          91      --      100   100   100                                  122          0       --      100   100   100                                  123          100     --      100   100   100                                  124          50      100     100   100   --                                   125          75      92      100   100   --                                   126          100     --      100   0     0                                    127          100     86      100   0     100                                  128          0       92      100   0     0                                    129          0       100     100   0     --                                   130          0       100     90    100   --                                   131          0       100     100   --    0                                    132          100     100     100   --    0                                    133          100     92      100   --    100                                  134                                                                           ______________________________________                                         *Dosage rate 500 ppm                                                     

EXAMPLE 8

The compounds indicated in Table 2 hereinbelow were tested on grapeplants for the preventative control of grape downy mildew caused byPlasmopara viticola.

In this test, 5 to 6 week old Vitis vinifera "Emperor" grape seedlingswere sprayed with a 716 micromolar aqueous solution of the test compoundcontaining a small amount of acetone or acetone and water (50:50% byvol.) or dimethylformamide to aid solubility and a nonionic emulsifier.The plants were then placed in an environmental chamber and inoculatedwith the organisms and returned in the chamber for two days to ensureinfection. The plants were then placed in standing water in a greenhousemaintained between 86° F. and 72° F. and relative humidity of 100% forten days. The plants are then evaluated for disease development. Four tosix plants were used for each test compound and evaluated againstuntreated plants (checks). Six check plants were used for each compoundgroup tested. The percent disease control afforded by a given compoundis based on the average disease reduction observed in the plants treatedwith the compound relative to the check plant average. These results arereported in Table 2 below. (Compound numbers refer to the compoundnumber assigned the compound in Table A hereinabove.)

                  TABLE 2                                                         ______________________________________                                        Preventative Control of Grape Downy Mildew                                    (Dosage rate 716μ molar unless otherwise indicated)                        COMPOUND  %           COMPOUND    %                                           NO.       CONTROL     NO.         CONTROL                                     ______________________________________                                        17         98         60          100                                         18        100         61          100                                         20        100         78           94                                         24        100         92           86                                         26        100         97          100                                         29        100         99*          91                                         30        100         104**        83                                         35        100         110         100                                         36         91         116          90                                         39         94         119          83                                         40        100         123**       100                                         43        100         124**        0                                          53         98         126**       100                                         54        100         127**       100                                         56         94         129**       100                                         57         56         130**       100                                                               131**       100                                                               132**       100                                                               133**       100                                                               134**       100                                         ______________________________________                                         *Dosage rate: 625μ molar.                                                  **Dosage rate: 200 ppm.                                                  

Obviously, many modifications and variations in the invention, describedhereinabove and below, can be made without departing from the essenceand scope thereof.

EXAMPLE 9

The compounds indicated in Table 3 hereinbelow were tested on Horsebeanplants for the preventative control of Chocolate spot, induced byBotrytis cineria.

In this test, 2 to three week old Horsebean (Vicia fava "Longacre")plants were sprayed with a 625 micromolar aqueous solution of the testcompound formulated in acetone, water, and a small amount on non-ionicsurfactant. The following day, plants were inoculated with a sporesuspension of the test fungus and placed in an environmental chambermaintained at 65° F and 100% relative humidity. After three days, plantswere evaluated for disease development. Four to six plants were used foreach test compound and were evaluated against untreated plants (checks).Four to six check plants were used for each compound group tested. Thepercent disease control afforded by a given test compound is based onthe average disease reduction observed in the plants treated with thecompound relative to the untreated check plant average. The results arereported in Table 3 below. (Compound numbers refer to the compoundnumber assigned the compound in Table A hereinabove).

                  TABLE 3                                                         ______________________________________                                        Preventative Control of Botrytis cineria                                      Induced Chocolate Spot in Beans                                               (Dosage rate 625 micromolar unless otherwise indicated)                       COMPOUND  %           COMPOUND    %                                           NO.       CONTROL     NO.         CONTROL                                     ______________________________________                                        29        100          71          70                                         33        100          72          0                                          34         97          97         100                                         37        100          98          80                                         40        100         100         100                                         41        100         101         100                                         42        100         103          68                                         44        100         108         100                                         45        100         112         100                                         46        100         115          95                                         48        100         116         100                                         66         85         118          0                                          67         70         131          0                                          68         93         132         100                                         69         90         133         100                                         70         90         134         100                                         ______________________________________                                    

Obviously, many modifications and variations in the invention, describedhereinabove and below, can be made without departing from the essenceand scope thereof.

What is claimed is:
 1. A process for preparing a compound having theformula ##STR22## wherein: R is alkyl having 1 through 4 carbon atoms;cycloalkyl having 3 through 6 carbon atoms; alkenyl having 2 through 6carbon atoms; haloalkyl having 1 through 4 halo substituentsindependently selected from the group of fluoro, chloro and bromo; orhaloalkenyl having 3 through 6 carbon atoms and 1 through 4 halo atomsindependently selected from the group of fluoro, chloro, and bromo;R¹ ishydrogen; alkyl having 1 through 12 carbon atoms; cycloalkyl having 3through 6 carbon atoms; lower alkenyl having 2 through 6 carbon atoms;haloalkyl having 1 through 4 carbon atoms and 1 through 3 halo atomsindependently selected from the group of fluoro, chloro, bromo, andiodo; haloalkenyl having 2 through 6 carbon atoms and 1 though 3 haloatoms independently selected from the group of fluoro, chloro, bromo,and iodo; cyanoalkyl wherein the alkyl moiety has 1 through 4 carbonatoms; hydroxyalkyl having 1 through 6 carbon atoms and 1 hydroxy group;lower alkoxyalkyl having 1 through 3 carbon atoms in the alkoxy moietyand 1 through 3 carbon atoms in the alkyl moiety; loweralkoxycarbonylalkyl having 1 through 3 carbon atoms in the alkoxy moietyand 1 through 3 carbon atoms in the alkyl moiety; phenyl; substitutedphenyl having 1 through 4 substituents independently selected from thegroup of fluoro, chloro, bromo, iodo, lower alkyl having 1 through 6carbon atoms and nitro with the proviso that said substituted phenyl hasno more than two nitro substituents; aralkyl having 1 through 4 carbonatoms in the alkyl moiety and wherein the aryl moiety is phenyl;substituted benzyl having 1 through 4 substituents on the phenyl moietyindependently selected from the group of fluoro, chloro, bromo, iodo,lower alkyl having 1 through 6 carbon atoms and nitro with the provisothe said phenyl moiety can have no more than 2 nitro substituents; and1,3-dioxolan-2-yl-alkyl in which the alkyl moiety has 1 through 4 carbonatoms; R² is hydrogen; lower alkyl having 1 through 6 carbon atoms;phenyl, benzyl, or substituted benzyl having 1 though 4 substituents onthe phenyl ring independently selected from the group of fluoro, chloro,bromo, iodo and alkyl, having 1 through 6 carbon atoms; R³ is hydrogenor alkyl having 1 through 6 carbon atoms with the proviso that when R⁴is other than alkyl then R³ is hydrogen; R⁴ is hydrogen, alkyl having 1through 6 carbon atoms, phenyl, or phenalkyl in which the alkyl moietyhas 1 through 4 carbon atoms; with the proviso that at least two of R¹,R², R³ and R⁴ are hydrogen and with the further proviso that when R³ isalkyl, then R⁴ is the identical parallel alkyl group; and X and Y areindependently hydrogen; alkyl having 1 through 4 carbon atoms; fluoro;chloro; alkoxy having 1 through 4 carbon atoms; alkylthio having 1through 4 carbon atoms; or haloalkyl having 1 through 4 carbon atoms and1 through 3 halo substituents independently selected from the group offluoro, chloro, and bromo; and may be located at any available positionof the respective phenyl rings; which comprises contacting a compoundhaving the formula ##STR23## wherein R, X and Y are as defined in claim1; R⁵ and R⁶ are independently hydrogen or lower alkyl; and Z ischloride, bromide or iodide; with a compound having the formula##STR24## wherein R¹, R², R³ and R⁴ are as defined hereinabove; underreactive conditions at temperatures in the range of about 20° C. to 35°C.
 2. The process of claim 1 wherein the compound of formula (II) iscontacted with the compound of formula C in an inert organic solvent. 3.The process of claim 1 wherein X and Y are identical parallelsubstituents located at the same position of the respective phenyl ringsto which they are attached.
 4. The process of claim 3 wherein R², R³ andR⁴ are each hydrogen
 5. The process of claim 3 wherein R is alkyl,alkenyl or haloalkenyl.
 6. The process of claim 3 wherein X and Y areeach hydrogen.
 7. The process of claim 6 wherein R², R³ and R⁴ are eachhydrogen.
 8. The process of claim 6 wherein R¹ is propyl, isopropyl,sec-butyl, 2-hydroxyethyl, t-butyl, cyclopropyl, vinyl, isopropenyl or2,2,2-trifluoromethyl.
 9. The process of claim 8 wherein R², R³ and R⁴are each hydrogen.
 10. The process of claim 8 wherein R is methyl orvinyl.
 11. A compound having the formula ##STR25## wherein R is alkylhaving 1 through 4 carbon atoms; cycloalkyl having 3 through 6 carbonatoms; alkenyl having 2 through 6 carbon atoms; haloalkyl having 1through 4 halo substituents independently selected from the group offluoro, chloro and bromo; or haloalkenyl having 3 through 6 carbon atomsand 1 through 4 halo atoms independently selected from the group offluoro, chloro, and bromo;R⁵ and R⁶ are independently hydrogen or loweralkyl having 1 through 6 carbon atoms; and X and Y are independentlyhydrogen; alkyl having 1 through 4 carbon atoms; fluoro; chloro; alkoxyhaving 1 through 4 carbon atoms; alkylthio having 1 through 4 carbonatoms; or haloalkyl having 1 through 4 carbon atoms and 1 through 3 halosubstituents independently selected from the group of fluoro, chloro,and bromo; and may be located at any available position of therespective phenyl rings.
 12. The compound of claim 1 wherein X and Y areidentical parallel substituents located at the same position of therespective phenyl rings to which they are attached.
 13. The compound ofclaim 1 wherein R⁵ and R⁶ are independently hydrogen or methyl.
 14. Thecompound of claim 11 wherein R is alkyl, alkenyl, or haloalkenyl. 15.The compound of claim 14 wherein R is methyl or vinyl.
 16. The compoundof claim 12 wherein R is alkyl, alkenyl, or haloalkenyl.
 17. Thecompound of claim 16 wherein R is methyl or vinyl.
 18. The compound ofclaim 12 wherein X and Y are each hydrogen.
 19. The compound of claim 18wherein R is alkyl, alkenyl, or haloalkenyl.
 20. The compound of claim18 wherein R is methyl or vinyl.